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

Base Information

• Chemical Name: (2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester
• CAS No.: 1000981-25-8
• Molecular Formula: C₃₈H₅₀N₂O₆Si
• Molecular Weight: 658.91
• Mol file: 1000981-25-8.mol

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

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

There total 7 articles about (2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-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: 63.0%

(2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-7-phenyl-hept-2-enoic acid ethyl ester (1000981-24-7) + N-Cbz-L-Phe (1161-13-3) → (2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester (1000981-25-8)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 7.5h; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.bmc.2018.07.015

Reference yield:

phenylbutyric acid chloride (18496-54-3) → (2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester (1000981-25-8)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere

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

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

4: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / Inert atmosphere; Cooling with ice

5: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

6: dmap / dichloromethane / 7.5 h / 20 °C / Inert atmosphere; Cooling with ice

With 2,6-dimethylpyridine; dmap; chloro-trimethyl-silane; magnesium bromide diethyl etherate; diphenyl phosphoryl azide; dihydrogen peroxide; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 1: |Evans Aldol Reaction / 2: |Evans Aldol Reaction;

DOI:10.1016/j.bmc.2018.07.015

Reference yield:

1-[(4S)-4-benzyl-2-thioxo-thiazolidin-3-yl]-4-phenyl-butan-1-one (1000981-16-7) → (2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-(tert-butyl-dimethylsilanyloxy)-7-phenyl-hept-2-enoic acid ethyl ester (1000981-25-8)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / Inert atmosphere; Cooling with ice

4: diphenyl phosphoryl azide; triethylamine / toluene / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

5: dmap / dichloromethane / 7.5 h / 20 °C / Inert atmosphere; Cooling with ice

With 2,6-dimethylpyridine; dmap; chloro-trimethyl-silane; magnesium bromide diethyl etherate; diphenyl phosphoryl azide; dihydrogen peroxide; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 1: |Evans Aldol Reaction;

DOI:10.1016/j.bmc.2018.07.015

upstream raw materials:

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

N-Cbz-L-Phe

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

phenylbutyric acid chloride

Downstream raw materials:

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