(2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester

Base Information

• Chemical Name: (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester
• CAS No.: 1092555-15-1
• Molecular Formula: C₃₂H₄₃NO₄S₂Si
• Molecular Weight: 597.915
• Mol file: 1092555-15-1.mol

Synonyms:(2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester

Chemical Property of (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester

There total 6 articles about (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester (1000981-18-9) + t-butyldimethylsiyl triflate (69739-34-0) → (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester (1092555-15-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -70 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.bmc.2018.07.015

Reference yield: 94.0%

tert-butyldimethylsilyl 2-methylpropane-2-sulfonate (1027156-11-1) + (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester (1000981-18-9) → (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester (1092555-15-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -70 ℃; for 6h; Inert atmosphere;

DOI:10.1002/cmdc.201500204

Reference yield:

(S)-4-benzylthiazolidin-2-thione (171877-39-7) → (2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester (1092555-15-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 24 h / 20 °C / Cooling with ice; Inert atmosphere

2: triethylamine; magnesium bromide ethyl etherate; chloro-trimethyl-silane / ethyl acetate / 288 h / 20 °C / Inert atmosphere

3: 2,6-dimethylpyridine / dichloromethane / 6 h / -70 °C / Inert atmosphere

With 2,6-dimethylpyridine; chloro-trimethyl-silane; magnesium bromide ethyl etherate; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1002/cmdc.201500204

upstream raw materials:

(2E,4R,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester

t-butyldimethylsiyl triflate

(S)-4-benzylthiazolidin-2-thione

phenylbutyric acid chloride

Downstream raw materials:

(2E,4R,5S)-4-(tert-butyl-dimethyl-silanyloxy)-5-phenethyl-hex-2-enedioic acid 1-ethyl ester

(2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-7-phenyl-hept-2-enoic acid ethyl ester

(2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester

(2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester