[(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester
• CAS No.: 158584-92-0
• Molecular Formula: C₂₇H₃₉NO₄Si
• Molecular Weight: 469.696
• Mol file: 158584-92-0.mol

Synonyms:[(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

Chemical Property of [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester

There total 8 articles about [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl 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:

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) → [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (158584-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / imidazole / dimethylformamide / 14 h / 25 °C

2: DIBALH / toluene / 0.5 h / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene;

Reference yield:

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tert-butyldiphenylsilyloxy)propanoate (171564-48-0) → [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (158584-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBALH / toluene / 0.5 h / -78 °C

With diisobutylaluminium hydride; In toluene;

Reference yield:

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) → [(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (158584-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / K₂CO₃ / dimethylformamide / 0 - 25 °C

2: 100 percent / imidazole / dimethylformamide / 14 h / 25 °C

3: DIBALH / toluene / 1.5 h / -78 °C

4: diethyl ether / 3.5 h / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; potassium carbonate; In diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00097a072

upstream raw materials:

(+)-diisopinocampheylallylborane

tert-butyl N-[(1R)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-ethyl]carbamate

allyl-trimethyl-silane

allylmagnesium bromide

Downstream raw materials:

(3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

(3R,4R)-3-Benzoylamino-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

(3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

(3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester