869898-86-2 (平板素,Platencin)

反应条件：

1.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; 25 °C; 25 °C → 40 °C; 40 min, 40 °C

参考文献：

Total Syntheses of (±)-Platencin and (-)-Platencin

Nicolaou, K. C.; et al, Journal of the American Chemical Society, 2009, 131(43), 15909-15917

合成路线：1 步

1020070-63-6

_93%

反应条件：

1.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt; rt → 40 °C; 40 min, 40 °C

参考文献：

Total synthesis of platencin

Nicolaou, K. C.; et al, Angewandte Chemie, 2008, 47(9), 1780-1783

合成路线：1 步

1020070-63-6

_90%

反应条件：

1.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt → 40 °C; 40 min, 40 °C; 40 °C → rt
1.2 Reagents: Sodium chloride Solvents: Water

参考文献：

Total Synthesis and Biological Evaluation of the Fab-Inhibitory Antibiotic Platencin and Analogues Thereof

Leung, Gulice Y. C.; et al, European Journal of Organic Chemistry, 2011, (1), 183-196

合成路线：1 步

860505-23-3

_58%

反应条件：

1.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide , 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, rt
1.2 Solvents: Dimethylformamide ; 40 h, rt

参考文献：

A Nine-Step Total Synthesis of (-)-Platencin

Tiefenbacher, Konrad; et al, Journal of Organic Chemistry, 2009, 74(8), 2937-2941

合成路线：1 步

860505-23-3

_42%

参考文献：

A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Muhammad, Rehmani N.; et al, Synlett, 2016, 27(1), 61-66

合成路线：1 步

860505-23-3

_42%

反应条件：

1.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, 18 °C
1.2 Solvents: Dimethylformamide ; 70 h, 18 °C

参考文献：

A Chemoenzymatic and Fully Stereocontrolled Total Synthesis of the Antibacterial Natural Product (-)-Platencin

Chang, Ee Ling; et al, Chemistry - An Asian Journal, 2015, 10(2), 427-439

合成路线：1 步

参考文献：

Enantioselective divergent approaches to both (-)-platensimycin and (-)-platencin

Hirai, Sho; et al, Tetrahedron, 2011, 67(2), 518-530

合成路线：1 步

1045821-33-7

参考文献：

Stereocontrolled Formal Synthesis of Platencin

Hsu, Day-Shin ; et al, European Journal of Organic Chemistry, 2018, 2018(34), 4689-4695

合成路线：2 步

1020070-44-3

反应条件：

1.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, 25 °C
2.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; 25 °C; 25 °C → 40 °C; 40 min, 40 °C

参考文献：

Total Syntheses of (±)-Platencin and (-)-Platencin

Nicolaou, K. C.; et al, Journal of the American Chemical Society, 2009, 131(43), 15909-15917

合成路线：2 步

1020070-44-3

反应条件：

1.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, rt
2.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt; rt → 40 °C; 40 min, 40 °C

参考文献：

Total synthesis of platencin

Nicolaou, K. C.; et al, Angewandte Chemie, 2008, 47(9), 1780-1783

合成路线：2 步

1193346-48-3

1020070-44-3

反应条件：

1.1 Reagents: Lithium hydroxide Solvents: Methanol , Water ; rt → 50 °C; 5 h, 50 °C
1.2 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 14 h, rt
1.3 Reagents: Sodium chloride Solvents: Water
2.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt → 40 °C; 40 min, 40 °C; 40 °C → rt
2.2 Reagents: Sodium chloride Solvents: Water

参考文献：

Total Synthesis and Biological Evaluation of the Fab-Inhibitory Antibiotic Platencin and Analogues Thereof

Leung, Gulice Y. C.; et al, European Journal of Organic Chemistry, 2011, (1), 183-196

合成路线：2 步

1135467-53-6

反应条件：

1.1 Reagents: Sodium bicarbonate Solvents: Tetrahydrofuran , Water ; 48 h, 18 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ; acidified
2.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, 18 °C
2.2 Solvents: Dimethylformamide ; 70 h, 18 °C

参考文献：

A Chemoenzymatic and Fully Stereocontrolled Total Synthesis of the Antibacterial Natural Product (-)-Platencin

Chang, Ee Ling; et al, Chemistry - An Asian Journal, 2015, 10(2), 427-439

合成路线：2 步

1135467-53-6

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; 23 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; acidified
2.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide , 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, rt
2.2 Solvents: Dimethylformamide ; 40 h, rt

参考文献：

A Nine-Step Total Synthesis of (-)-Platencin

Tiefenbacher, Konrad; et al, Journal of Organic Chemistry, 2009, 74(8), 2937-2941

合成路线：2 步

1172604-42-0

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water ; 4 h, rt
2.1 -

参考文献：

Stereocontrolled Formal Synthesis of Platencin

Hsu, Day-Shin ; et al, European Journal of Organic Chemistry, 2018, 2018(34), 4689-4695

合成路线：2 步

1193346-48-3

反应条件：

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; 0.5 h, 18 °C
2.1 -

参考文献：

A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Muhammad, Rehmani N.; et al, Synlett, 2016, 27(1), 61-66

合成路线：3 步

1193346-48-3

反应条件：

1.1 Reagents: Lithium hydroxide Solvents: Methanol , Water ; 25 °C; 25 °C → 50 °C; 6 h, 50 °C
2.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, 25 °C
3.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; 25 °C; 25 °C → 40 °C; 40 min, 40 °C

参考文献：

Total Syntheses of (±)-Platencin and (-)-Platencin

Nicolaou, K. C.; et al, Journal of the American Chemical Society, 2009, 131(43), 15909-15917

合成路线：2 步

1252021-88-7

反应条件：

1.1 Solvents: Dichloromethane ; rt
1.2 Reagents: Dess-Martin periodinane ; 1 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ; rt
1.4 Reagents: Sodium thiosulfate Solvents: Water ; rt
2.1 -

参考文献：

Enantioselective divergent approaches to both (-)-platensimycin and (-)-platencin

Hirai, Sho; et al, Tetrahedron, 2011, 67(2), 518-530

合成路线：3 步

1020070-61-4

反应条件：

1.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; 20 min, 25 °C
2.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, 25 °C
3.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; 25 °C; 25 °C → 40 °C; 40 min, 40 °C

参考文献：

Total Syntheses of (±)-Platencin and (-)-Platencin

Nicolaou, K. C.; et al, Journal of the American Chemical Society, 2009, 131(43), 15909-15917

合成路线：3 步

1020070-61-4

反应条件：

1.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; 20 min, rt
2.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, rt
3.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt; rt → 40 °C; 40 min, 40 °C

参考文献：

Total synthesis of platencin

Nicolaou, K. C.; et al, Angewandte Chemie, 2008, 47(9), 1780-1783

合成路线：3 步

1020070-68-1

1663-39-4

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol , Tetrahydrofuran ; rt; 15 min, rt
1.2 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ; 20 min, rt
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Lithium hydroxide Solvents: Methanol , Water ; rt → 50 °C; 5 h, 50 °C
2.2 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 14 h, rt
2.3 Reagents: Sodium chloride Solvents: Water
3.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt → 40 °C; 40 min, 40 °C; 40 °C → rt
3.2 Reagents: Sodium chloride Solvents: Water

参考文献：

Total Synthesis and Biological Evaluation of the Fab-Inhibitory Antibiotic Platencin and Analogues Thereof

Leung, Gulice Y. C.; et al, European Journal of Organic Chemistry, 2011, (1), 183-196

合成路线：4 步

1020070-68-1

1663-39-4

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol , Tetrahydrofuran ; 25 °C; 15 min, 25 °C
1.2 Solvents: Tetrahydrofuran ; 30 min, 25 °C
1.3 Reagents: Ammonium chloride Solvents: Water ; 25 °C
2.1 Reagents: Lithium hydroxide Solvents: Methanol , Water ; 25 °C; 25 °C → 50 °C; 6 h, 50 °C
3.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, 25 °C
4.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; 25 °C; 25 °C → 40 °C; 40 min, 40 °C

参考文献：

Total Syntheses of (±)-Platencin and (-)-Platencin

Nicolaou, K. C.; et al, Journal of the American Chemical Society, 2009, 131(43), 15909-15917

合成路线：3 步

1020070-68-1

96-33-3

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: Diethyl ether , tert-Butanol ; 5 min, 0 °C
1.2 30 min, 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; 23 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; acidified
3.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide , 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, rt
3.2 Solvents: Dimethylformamide ; 40 h, rt

参考文献：

A Nine-Step Total Synthesis of (-)-Platencin

Tiefenbacher, Konrad; et al, Journal of Organic Chemistry, 2009, 74(8), 2937-2941

合成路线：3 步

1020070-69-2

反应条件：

1.1 Reagents: Acetic acid , Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate ; 16 h, 25 °C
2.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, 25 °C
3.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; 25 °C; 25 °C → 40 °C; 40 min, 40 °C

参考文献：

Total Syntheses of (±)-Platencin and (-)-Platencin

Nicolaou, K. C.; et al, Journal of the American Chemical Society, 2009, 131(43), 15909-15917

合成路线：3 步

1020070-69-2

反应条件：

1.1 Reagents: Acetic acid , Hydrogen Catalysts: Palladium Solvents: Methanol , Ethyl acetate ; 16 h, rt
2.1 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 13 h, rt
3.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt; rt → 40 °C; 40 min, 40 °C

参考文献：

Total synthesis of platencin

Nicolaou, K. C.; et al, Angewandte Chemie, 2008, 47(9), 1780-1783

合成路线：3 步

1779-49-3

1252021-87-6

反应条件：

1.1 Solvents: Tetrahydrofuran ; rt → 0 °C
1.2 Reagents: Butyllithium Solvents: Hexane ; 10 min, 0 °C
1.3 Solvents: Toluene ; 0 °C; 0 °C → 50 °C; 1.5 h, 50 °C; 50 °C → rt
1.4 Reagents: Ammonium chloride Solvents: Water
1.5 Solvents: Tetrahydrofuran ; rt
1.6 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; rt → 60 °C; 1 h, 60 °C; 60 °C → rt
1.7 Reagents: Ammonium chloride Solvents: Water ; rt
2.1 Solvents: Dichloromethane ; rt
2.2 Reagents: Dess-Martin periodinane ; 1 h, rt
2.3 Reagents: Sodium bicarbonate Solvents: Water ; rt
2.4 Reagents: Sodium thiosulfate Solvents: Water ; rt
3.1 -

参考文献：

Enantioselective divergent approaches to both (-)-platensimycin and (-)-platencin

Hirai, Sho; et al, Tetrahedron, 2011, 67(2), 518-530

合成路线：3 步

3487-44-3

1265279-22-8

反应条件：

1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ; 0.75 h, 18 °C; 18 °C → 78 °C
1.2 Solvents: Tetrahydrofuran ; 1 h, -78 °C; -78 °C → 18 °C; 1.5 h, 18 °C
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ; 0.5 h, 18 °C
3.1 -

参考文献：

A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Muhammad, Rehmani N.; et al, Synlett, 2016, 27(1), 61-66

合成路线：3 步

1674392-58-5

反应条件：

1.1 Reagents: Chlorotrimethylsilane , Lithium bis(trimethylsilyl)amide Solvents: Dichloromethane ; 1 h, 18 °C
1.2 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Dimethyl sulfoxide , N-methylmorpholine N-oxide ; 16 h, 60 °C
2.1 Reagents: Sodium bicarbonate Solvents: Tetrahydrofuran , Water ; 48 h, 18 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; acidified
3.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, 18 °C
3.2 Solvents: Dimethylformamide ; 70 h, 18 °C

参考文献：

A Chemoenzymatic and Fully Stereocontrolled Total Synthesis of the Antibacterial Natural Product (-)-Platencin

Chang, Ee Ling; et al, Chemistry - An Asian Journal, 2015, 10(2), 427-439

合成路线：3 步

2243569-36-8

反应条件：

1.1 Reagents: Formic acid Solvents: Tetrahydrofuran , Water ; 0 °C; 5 min, 0 °C; 7 h, rt
1.2 Reagents: Sodium carbonate Solvents: Water ; rt
2.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water ; 4 h, rt
3.1 -

参考文献：

Stereocontrolled Formal Synthesis of Platencin

Hsu, Day-Shin ; et al, European Journal of Organic Chemistry, 2018, 2018(34), 4689-4695

合成路线：4 步

74-88-4

反应条件：

1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Toluene , Tetrahydrofuran , Hexamethylphosphoramide ; 30 min, -78 °C
1.2 2 h, -78 °C; 1 h, -78 °C → 0 °C
1.3 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Potassium tert-butoxide Solvents: tert-Butanol , Tetrahydrofuran ; rt; 15 min, rt
2.2 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ; 20 min, rt
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Lithium hydroxide Solvents: Methanol , Water ; rt → 50 °C; 5 h, 50 °C
3.2 Reagents: Triethylamine , O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate Solvents: Dimethylformamide ; 14 h, rt
3.3 Reagents: Sodium chloride Solvents: Water
4.1 Reagents: Methanaminium, N-[bis(dimethylamino)-λ4-sulfanylidene]-N-methyl-, difluorotrimet… Solvents: Dimethylformamide ; rt → 40 °C; 40 min, 40 °C; 40 °C → rt
4.2 Reagents: Sodium chloride Solvents: Water

参考文献：

Total Synthesis and Biological Evaluation of the Fab-Inhibitory Antibiotic Platencin and Analogues Thereof

Leung, Gulice Y. C.; et al, European Journal of Organic Chemistry, 2011, (1), 183-196

合成路线：4 步

74-88-4

反应条件：

1.1 Reagents: Hexamethylphosphoramide , Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ; -78 °C
2.1 Reagents: Potassium tert-butoxide Solvents: Diethyl ether , tert-Butanol ; 5 min, 0 °C
2.2 30 min, 0 °C
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; 23 h, rt
3.2 Reagents: Hydrochloric acid Solvents: Water ; acidified
4.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide , 4-(Dimethylamino)pyridine Solvents: Acetonitrile , Dichloromethane ; 7.5 h, rt
4.2 Solvents: Dimethylformamide ; 40 h, rt

参考文献：

A Nine-Step Total Synthesis of (-)-Platencin

Tiefenbacher, Konrad; et al, Journal of Organic Chemistry, 2009, 74(8), 2937-2941

合成路线：5 步

74-88-4