884600-68-4 ((GSM-1)

快速询单

结构式：

GSM-1MOL文件

CAS号：

884600-68-4

英文名称：

GSM-1

分子式：

C₂₆H₃₁ClF₃NO₂

分子量：

481.978057146072

简介：

GSM-1 是有效的 γ-secretase 调节剂。GSM-1 直接靶向早衰蛋白 1 (PS1) 的跨膜结构域。

GSM-1(884600-68-4)名称与标识符

名称

英文别名：

4-Piperidineacetic acid,1-[(1R)-1-(4-chlorophenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]-,(2S,4R)-;GSM-1;(2S,4R)-1-[(1R)-1-(4-Chlorophenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]-4-piperidineacetic acid (ACI);GSM 1;GSM 1 (enzyme modulator);γ Secretase modulator 1;

标识符

InChIKey：

VMVWLAPASRQXFL-QFWMQHCXSA-N

Inchi：

1S/C26H31ClF3NO2/c1-17(2)3-12-23(19-6-10-22(27)11-7-19)31-14-13-18(16-25(32)33)15-24(31)20-4-8-21(9-5-20)26(28,29)30/h4-11,17-18,23-24H,3,12-16H2,1-2H3,(H,32,33)/t18-,23-,24+/m1/s1

SMILES：

[C@@H](C1C=CC(Cl)=CC=1)(N1CC[C@@H](CC(=O)O)C[C@H]1C1C=CC(C(F)(F)F)=CC=1)CCC(C)C

GSM-1(884600-68-4)推荐厂家更多厂家(2)

公司名称	手机号/电话	联系人	QQ	微信	询单
MedChemExpress（MCE 中国）	13611715263 021-58955995	MCE生命科学试剂	2881321772		询单
上海源溪生物科技有限公司	13564518121	李经理	1724405207		询单

GSM-1(884600-68-4)合成路线

合成路线：1 步

2723502-31-4

_65%

884600-68-4

反应条件：

1.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：2 步

反应条件：

1.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
1.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
2.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：3 步

2723502-02-9

884600-68-4

反应条件：

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ; 0 °C; 12 h, 0 °C
2.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
2.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
3.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
3.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：4 步

2723502-08-5

884600-68-4

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 0 °C; 1 h, rt
1.2 Reagents: Potassium carbonate Solvents: Ethanol ; 12 h, rt
2.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ; 0 °C; 12 h, 0 °C
3.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
3.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
4.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
4.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：5 步

2723502-15-4

884600-68-4

反应条件：

1.1 Reagents: Lithium tri-sec-butylborohydride Solvents: Tetrahydrofuran ; -78 °C; 12 h, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 0 °C; 1 h, rt
2.2 Reagents: Potassium carbonate Solvents: Ethanol ; 12 h, rt
3.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ; 0 °C; 12 h, 0 °C
4.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
4.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
5.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
5.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：6 步

2723502-21-2

196929-78-9

884600-68-4

反应条件：

1.1 Reagents: Titanium ethoxide Solvents: Tetrahydrofuran ; reflux
2.1 Reagents: Lithium tri-sec-butylborohydride Solvents: Tetrahydrofuran ; -78 °C; 12 h, -78 °C
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 0 °C; 1 h, rt
3.2 Reagents: Potassium carbonate Solvents: Ethanol ; 12 h, rt
4.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ; 0 °C; 12 h, 0 °C
5.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
5.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
6.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
6.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：7 步

106263-53-0

2049-67-4

884600-68-4

反应条件：

1.1 Reagents: Sodium ethoxide Solvents: Ethanol ; 0.5 h, rt; 24 h, 50 °C
1.2 Reagents: Ammonium chloride Solvents: Water
1.3 Reagents: Sodium chloride Solvents: Dimethylacetamide ; rt; 16 h, 160 °C
2.1 Reagents: Titanium ethoxide Solvents: Tetrahydrofuran ; reflux
3.1 Reagents: Lithium tri-sec-butylborohydride Solvents: Tetrahydrofuran ; -78 °C; 12 h, -78 °C
3.2 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 0 °C; 1 h, rt
4.2 Reagents: Potassium carbonate Solvents: Ethanol ; 12 h, rt
5.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ; 0 °C; 12 h, 0 °C
6.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
6.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
7.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
7.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：7 步

2723502-26-7

884600-68-4

反应条件：

1.1 Reagents: Sodium chloride Solvents: Dimethylacetamide ; rt; 16 h, 160 °C
2.1 Reagents: Titanium ethoxide Solvents: Tetrahydrofuran ; reflux
3.1 Reagents: Lithium tri-sec-butylborohydride Solvents: Tetrahydrofuran ; -78 °C; 12 h, -78 °C
3.2 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 0 °C; 1 h, rt
4.2 Reagents: Potassium carbonate Solvents: Ethanol ; 12 h, rt
5.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ; 0 °C; 12 h, 0 °C
6.1 Reagents: 1H-Benzotriazole Solvents: Toluene ; 18 h, reflux
6.2 Reagents: Zinc chloride Solvents: Diethyl ether ; 0 °C; 1 h, rt
7.1 Reagents: Lithium hydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 0 °C; 16 h, rt
7.2 Reagents: Hydrochloric acid Solvents: Water ; pH 7

参考文献：

A Local Desymmetrization Approach to Piperidinyl Acetic Acid γ-Secretase Modulators

Cheng, Peng; et al, Journal of Organic Chemistry, 2021, 86(21), 15481-15487

合成路线：1 步

884603-33-2

884600-68-4

1217267-66-7

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：2 步

1996657-20-5

884600-68-4

1217267-66-7

反应条件：

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
1.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
1.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
2.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：2 步

1996657-21-6

884600-68-4

1217267-66-7

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
2.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：3 步

反应条件：

1.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
2.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
2.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
2.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
3.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：4 步

反应条件：

1.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
2.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
3.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
3.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
3.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
4.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：5 步

1996657-06-7

884600-68-4

1217267-66-7

反应条件：

1.1 Reagents: Ammonium hydroxide Solvents: Acetonitrile , Water ; 1 min, 25 °C; 1 h, 25 °C
1.2 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride , Acetonitrile , Water ; 14 h, 25 °C
2.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
3.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
4.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
4.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
4.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
5.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：5 步

1996657-17-0

884600-68-4

1217267-66-7

反应条件：

1.1 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride , Acetonitrile , Water ; 14 h, 25 °C
2.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
3.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
4.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
4.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
4.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
5.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：6 步

反应条件：

1.1 Catalysts: (4R)-4-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-L-proline Solvents: Water ; 44 h, 25 °C
1.2 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane , Water ; 5 min, 25 °C; 9 h, 25 °C
1.3 Reagents: Sodium sulfite Solvents: Water
2.1 Reagents: Ammonium hydroxide Solvents: Acetonitrile , Water ; 1 min, 25 °C; 1 h, 25 °C
2.2 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride , Acetonitrile , Water ; 14 h, 25 °C
3.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
4.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
5.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
5.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
5.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
6.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：6 步

1996656-90-6

884600-68-4

1217267-66-7

反应条件：

1.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane , Water ; 5 min, 25 °C; 9 h, 25 °C
1.2 Reagents: Sodium sulfite Solvents: Water
2.1 Reagents: Ammonium hydroxide Solvents: Acetonitrile , Water ; 1 min, 25 °C; 1 h, 25 °C
2.2 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride , Acetonitrile , Water ; 14 h, 25 °C
3.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
4.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
5.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
5.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
5.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
6.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：7 步

1996656-75-7

884600-68-4

1217267-66-7

反应条件：

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Acetone , Water ; 10 h, 55 °C; 55 °C → 25 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ; 15 min, 25 °C
2.1 Catalysts: (4R)-4-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-L-proline Solvents: Water ; 44 h, 25 °C
2.2 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane , Water ; 5 min, 25 °C; 9 h, 25 °C
2.3 Reagents: Sodium sulfite Solvents: Water
3.1 Reagents: Ammonium hydroxide Solvents: Acetonitrile , Water ; 1 min, 25 °C; 1 h, 25 °C
3.2 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride , Acetonitrile , Water ; 14 h, 25 °C
4.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
5.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
6.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
6.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
6.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
7.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348

合成路线：8 步

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether , Hexane ; 15 min, -60 °C; -60 °C → -78 °C
1.2 Solvents: Diethyl ether ; 10 min, -78 °C; 4 h, -78 °C
1.3 Reagents: Water ; -78 °C
2.1 Catalysts: p-Toluenesulfonic acid Solvents: Acetone , Water ; 10 h, 55 °C; 55 °C → 25 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water ; 15 min, 25 °C
3.1 Catalysts: (4R)-4-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-L-proline Solvents: Water ; 44 h, 25 °C
3.2 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane , Water ; 5 min, 25 °C; 9 h, 25 °C
3.3 Reagents: Sodium sulfite Solvents: Water
4.1 Reagents: Ammonium hydroxide Solvents: Acetonitrile , Water ; 1 min, 25 °C; 1 h, 25 °C
4.2 Reagents: Sodium periodate Catalysts: Ruthenium trichloride Solvents: Carbon tetrachloride , Acetonitrile , Water ; 14 h, 25 °C
5.1 Reagents: 4-(Trifluoromethyl)benzoic acid Solvents: Diethyl ether , Methanol ; 5 min, cooled; 2 h, cooled
6.1 Reagents: Lead tetraacetate Solvents: tert-Butanol ; 5 min, 25 °C; 45 min, 78 °C
7.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; cooled; 1 h, cooled
7.2 Reagents: Sodium bicarbonate Solvents: Water ; cooled
7.3 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 14 h, 7 bar, 25 °C
8.1 -

参考文献：

Beyond Chemoselectivity: Catalytic Site-Selective Aldolization of Diketones and Exploitation for Enantioselective Alzheimer's Drug Candidate Synthesis

Nugent, Thomas C.; et al, Chemistry - A European Journal, 2016, 22(40), 14342-14348