(3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester

Base Information

• Chemical Name: (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester
• CAS No.: 300699-05-2
• Molecular Formula: C₂₅H₃₅NO₆Si
• Molecular Weight: 473.642
• Mol file: 300699-05-2.mol

Synonyms:(3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester

Chemical Property of (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester

There total 4 articles about (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl 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-phenoxy-1-trimethylsilyloxyethene (111061-31-5) + [(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester (154161-01-0) → (3R,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester + (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester (300699-05-2)

Guidance literature:

With (S)-oxazaborolidinone; In dichloromethane; at -78 ℃; for 24h;

DOI:10.1016/S0040-4039(00)01124-2

Reference yield:

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester (300699-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 2,6-lutidine / CH₂Cl₂

2: 80 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: (S)-oxazaborolidinone / CH₂Cl₂ / 24 h / -78 °C

With 2,6-dimethylpyridine; (S)-oxazaborolidinone; diisobutylaluminium hydride; In dichloromethane; 1: silylation / 2: Reduction / 3: Addition;

DOI:10.1016/S0040-4039(00)01124-2

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester (300699-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 2,6-lutidine / CH₂Cl₂

2: 80 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: (S)-oxazaborolidinone / CH₂Cl₂ / 24 h / -78 °C

With 2,6-dimethylpyridine; (S)-oxazaborolidinone; diisobutylaluminium hydride; In dichloromethane; 1: silylation / 2: Reduction / 3: Addition;

DOI:10.1016/S0040-4039(00)01124-2

upstream raw materials:

1-phenoxy-1-trimethylsilyloxyethene

[(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester

N-benzyloxycarbonyl-L-serine methyl ester

t-butyldimethylsiyl triflate

Downstream raw materials:

(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-5-phenoxycarbonylmethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-5-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(2-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((S)-3-ethoxycarbonyl-2-hydroxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester