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

Base Information

• Chemical Name: (2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-7-phenyl-hept-2-enoic acid ethyl ester
• CAS No.: 1000981-24-7
• Molecular Formula: C₂₂H₃₃NO₄Si
• Molecular Weight: 403.594
• Mol file: 1000981-24-7.mol

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

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

There total 5 articles about (2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-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: 60.0%

(2E,4R,5S)-4-(tert-butyl-dimethyl-silanyloxy)-5-phenethyl-hex-2-enedioic acid 1-ethyl ester (1000981-23-6) → (2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-7-phenyl-hept-2-enoic acid ethyl ester (1000981-24-7)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In toluene; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1002/cmdc.201500204

Reference yield:

(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) → (2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-7-phenyl-hept-2-enoic acid ethyl ester (1000981-24-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: triethylamine; diphenylphosphoranyl azide / toluene / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

With diphenylphosphoranyl azide; water; dihydrogen peroxide; triethylamine; lithium hydroxide; In tetrahydrofuran; toluene;

DOI:10.1002/cmdc.201500204

Reference yield:

1-[(4S)-4-benzyl-2-thioxo-thiazolidin-3-yl]-4-phenyl-butan-1-one (1000981-16-7) → (2E,4R,5S)-4-(tert-butyl-dimethylsilanyloxy)-5-isocyanato-7-phenyl-hept-2-enoic acid ethyl ester (1000981-24-7)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

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

With 2,6-dimethylpyridine; chloro-trimethyl-silane; diphenylphosphoranyl azide; water; dihydrogen peroxide; magnesium bromide ethyl etherate; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1002/cmdc.201500204

upstream raw materials:

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

phenylbutyric acid chloride

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

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

Downstream raw materials:

(2E,4R,5S)-5-[(2S)-2-benzyloxycarbonylamino-3-phenylpropionylamino]-4-(tert-butyl-dimethylsilanyloxy)-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