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

Base Information

• Chemical Name: (2E,4S,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester
• CAS No.: 1000981-17-8
• Molecular Formula: C₂₆H₂₉NO₄S₂
• Molecular Weight: 483.653
• Mol file: 1000981-17-8.mol

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

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

There total 4 articles about (2E,4S,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-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:

1-[(4S)-4-benzyl-2-thioxo-thiazolidin-3-yl]-4-phenyl-butan-1-one (1000981-16-7) + 4-oxo-but-2-enoic acid ethyl ester (2960-66-9) → (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,4S,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester (1000981-17-8)

Guidance literature:

1-[(4S)-4-benzyl-2-thioxo-thiazolidin-3-yl]-4-phenyl-butan-1-one; 4-oxo-but-2-enoic acid ethyl ester; With chloro-trimethyl-silane; magnesium bromide; In ethyl acetate;

With hydrogenchloride; In ethyl acetate; Further stages.;

DOI:10.1016/j.bmcl.2007.10.056

Reference yield:

C29H37NO4S2Si + C29H37NO4S2Si → (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,4S,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester (1000981-17-8)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;

Reference yield:

phenylbutyric acid chloride (18496-54-3) → (2E,4S,5S)-5-[(4S)-4-benzyl-2-thioxo-thiazolidine-3-carbonyl]-4-hydroxy-7-phenyl-hept-2-enoic acid ethyl ester (1000981-17-8)

Guidance literature:

Multi-step reaction with 2 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

With chloro-trimethyl-silane; magnesium bromide ethyl etherate; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1002/cmdc.201500204

upstream raw materials:

1-[(4S)-4-benzyl-2-thioxo-thiazolidin-3-yl]-4-phenyl-butan-1-one

4-oxo-but-2-enoic acid ethyl ester

(S)-4-benzylthiazolidin-2-thione

phenylbutyric acid chloride

Downstream raw materials:

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

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

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

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