84520-67-2 ((2S,4R)-Boc-γ-甲磺酰基氧甲基脯氨酸甲酯,(2S,4R)-Boc-γ-mso-proline methyl ester)

反应条件：

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 0 °C; 5 h, rt

参考文献：

Synthetic marine sponge collagen by late-stage dihydroxylation

Priem, Christoph; et al, Organic Letters, 2018, 20(1), 162-165

合成路线：1 步

74844-91-0

124-63-0

_100%

反应条件：

1.1 Solvents: Pyridine

参考文献：

Dideoxy nucleoside triphosphate (ddNTP) analogues: Synthesis and polymerase substrate activities of pyrrolidinyl nucleoside triphosphates (prNTPs)

Gade, Chandrasekhar Reddy; et al, Bioorganic & Medicinal Chemistry, 2016, 24(18), 4016-4022

合成路线：1 步

_93%

反应条件：

1.1 Reagents: Triethylamine Solvents: Dichloromethane ; rt → 0 °C; 5 min, 0 °C
1.2 Solvents: Dichloromethane ; 0 °C; 1 h, 0 °C
1.3 Reagents: Hydrogen ; 0 °C; 2 h, 8 - 10 °C

参考文献：

Synthesis of doripenem

Zhang, Aiyan; et al, Zhongguo Yiyao Gongye Zazhi, 2006, 37(6), 361-363

合成路线：1 步

_78%

反应条件：

1.1 Reagents: Thionyl chloride Solvents: Methanol ; 2 h, reflux; reflux → rt; overnight, rt; cooled
1.2 Reagents: Triethylamine , 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; cooled; overnight, rt
1.3 Solvents: Water ; rt; rt → 0 °C
1.4 Reagents: Triethylamine , 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 2 h, rt
1.5 Solvents: Water ; rt

参考文献：

Synthesis of 3'-Deoxy-3'-difluoromethyl Azanucleosides from trans-4-Hydroxy-L-proline

Qiu, Xiao-Long; et al, Journal of Organic Chemistry, 2005, 70(10), 3826-3837

合成路线：1 步

_65%

反应条件：

1.1 Reagents: Thionyl chloride Solvents: Methanol
1.2 Reagents: Triethylamine Solvents: Dichloromethane
1.3 Reagents: Triethylamine Solvents: Dichloromethane

参考文献：

Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A2 Receptor Antagonists

Marusawa, Hiroshi; et al, Bioorganic & Medicinal Chemistry, 2002, 10(5), 1399-1415

合成路线：1 步

参考文献：

Synthesis and antibacterial activity of 6(R)- and 6(S)-fluoropenibruguieramine A: Fluorine as a probe for testing the powerfulness of memory of chirality (MOC)

Liu, Ting; et al, Journal of Fluorine Chemistry, 2018, 207, 18-23

合成路线：2 步

334-88-3

反应条件：

1.1 Solvents: Diethyl ether , Methanol ; rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 3 h, 0 °C

参考文献：

Novel chemotactic For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold: Synthesis and bioactivity

Torino, Domenica; et al, Bioorganic & Medicinal Chemistry, 2009, 17(1), 251-259

合成路线：2 步

74-88-4

反应条件：

1.1 Reagents: Cesium carbonate Solvents: Dimethylformamide ; 15 h, rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 0.5 h, 0 °C
2.2 15 h, 0 °C → rt

参考文献：

Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction - vibrational spectroscopy distinguishes oxazolidinone from enamine species

Willms, J. Alexander; et al, Physical Chemistry Chemical Physics, 2019, 21(5), 2578-2586

合成路线：2 步

77-78-1

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ; 6 h, 56 °C
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 0 °C; 30 min, 0 °C

参考文献：

Multipodal insulin mimetics built on adamantane or proline scaffolds

Hajduch, Jan; et al, Bioorganic Chemistry, 2021, 107,

合成路线：2 步

77-78-1

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Acetone ; 12 h, reflux
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 1 h, 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; rt

参考文献：

Gold nanoparticle-based colorimetric chiral discrimination of histidine: application to determining the enantiomeric excess of histidine

Seo, Seong Hyeok; et al, Analytical Methods, 2014, 6(1), 73-76

合成路线：2 步

1499-56-5

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 30 min, rt
1.2 Solvents: 1,4-Dioxane , Water ; rt; 4 h, rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 30 min, rt
2.2 rt; 30 min, 0 - 5 °C

参考文献：

Antibacterial and anti-TB tat-peptidomimetics with improved efficacy and half-life

Bhosle, Govind S.; et al, European Journal of Medicinal Chemistry, 2018, 152, 358-369

合成路线：2 步

1499-56-5

反应条件：

1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; rt → 0 °C
1.2 Solvents: Dichloromethane ; 0 °C; 19 h, rt
2.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 0 °C; 5 h, rt

参考文献：

Synthetic marine sponge collagen by late-stage dihydroxylation

Priem, Christoph; et al, Organic Letters, 2018, 20(1), 162-165

合成路线：2 步

40216-83-9

反应条件：

1.1 Reagents: Triethylamine Solvents: Dichloromethane
2.1 Solvents: Dichloromethane , Pyridine ; 0 °C

参考文献：

Quinoline-Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

Ganesan, Moorthiamma Sarathy; et al, Journal of Heterocyclic Chemistry, 2021, 58(4), 952-968

合成路线：2 步

40216-83-9

反应条件：

1.1 Reagents: Triethylamine Solvents: Acetonitrile , Water
2.1 Solvents: Pyridine

参考文献：

Dideoxy nucleoside triphosphate (ddNTP) analogues: Synthesis and polymerase substrate activities of pyrrolidinyl nucleoside triphosphates (prNTPs)

Gade, Chandrasekhar Reddy; et al, Bioorganic & Medicinal Chemistry, 2016, 24(18), 4016-4022

合成路线：2 步

40216-83-9

反应条件：

1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ; overnight, rt
2.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ; 5 min, rt
2.2 0 °C; 2 h, rt

参考文献：

Bioactive gold(I) complexes with 4-mercapto proline derivatives

Gutierrez, Alejandro; et al, Dalton Transactions, 2016, 45(34), 13483-13490

合成路线：2 步

反应条件：

1.1 Reagents: Thionyl chloride Solvents: Methanol ; 0 °C; 8 h, rt
1.2 Reagents: Triethylamine Solvents: 1,4-Dioxane , Water ; basified, rt
1.3 10 h, rt
2.1 Reagents: Pyridine ; 0 °C; 2 h, 0 °C

参考文献：

C3'-endo-puckered pyrrolidine containing PNA has favorable geometry for RNA binding: Novel ethano locked PNA (ethano-PNA)

Banerjee, Anjan; et al, Bioorganic & Medicinal Chemistry, 2013, 21(14), 4092-4101

合成路线：2 步

反应条件：

1.1 Reagents: Thionyl chloride Solvents: Methanol
1.2 Reagents: Triethylamine Solvents: Dichloromethane ; overnight, rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; 4 h, rt

参考文献：

Synthesis of chiral pyrrolidine isostere inserted into pyrrole polyamide skeleton

Lin, Chun-Yu; et al, Journal of the Chinese Chemical Society (Weinheim, 2012, 59(3), 436-442

合成路线：3 步

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; overnight, rt
2.1 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ; 6 h, 56 °C
3.1 Reagents: Triethylamine Solvents: Dichloromethane ; 0 °C; 30 min, 0 °C

参考文献：

Multipodal insulin mimetics built on adamantane or proline scaffolds

Hajduch, Jan; et al, Bioorganic Chemistry, 2021, 107,

合成路线：3 步

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Methanol , Tetrahydrofuran ; 12 h, rt
1.2 Reagents: Potassium bisulfate Solvents: Ethyl acetate , Water ; pH 2, rt
2.1 Reagents: Potassium carbonate Solvents: Acetone ; 12 h, reflux
3.1 Reagents: Triethylamine Solvents: Dichloromethane ; 1 h, 0 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ; rt

参考文献：

Gold nanoparticle-based colorimetric chiral discrimination of histidine: application to determining the enantiomeric excess of histidine

Seo, Seong Hyeok; et al, Analytical Methods, 2014, 6(1), 73-76

合成路线：2 步

67-56-1

反应条件：

1.1 Reagents: Thionyl chloride Solvents: Methanol ; 0 °C; 0 °C → rt; 20 min, rt; rt → 40 °C; 14 h, 40 °C
2.1 Reagents: Triethylamine Solvents: Dichloromethane ; rt → 0 °C; 5 min, 0 °C
2.2 Solvents: Dichloromethane ; 0 °C; 1 h, 0 °C
2.3 Reagents: Hydrogen ; 0 °C; 2 h, 8 - 10 °C

参考文献：

Synthesis of doripenem

Zhang, Aiyan; et al, Zhongguo Yiyao Gongye Zazhi, 2006, 37(6), 361-363

合成路线：3 步

67-56-1