(2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one

Base Information

• Chemical Name: (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one
• CAS No.: 363610-59-7
• Molecular Formula: C₃₃H₄₁NO₄SSi
• Molecular Weight: 575.844
• Mol file: 363610-59-7.mol

Synonyms:(2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one

Chemical Property of (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one

There total 3 articles about (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one 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: 70.0%

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione (145588-95-0,334968-78-4) → (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one (363610-59-7)

Guidance literature:

With N,N-diethyl-N-isopropylamine; titanium tetrachloride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(01)00893-0

Reference yield:

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8) → (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one (363610-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 70 percent / TiCl₄; Et₂iPrN / CH₂Cl₂ / -78 °C

With oxalyl dichloride; N,N-diethyl-N-isopropylamine; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(01)00893-0

Reference yield:

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester (95514-03-7) → (2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one (363610-59-7)

Guidance literature:

Multi-step reaction with 3 steps

1: LiBH₄

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 70 percent / TiCl₄; Et₂iPrN / CH₂Cl₂ / -78 °C

With lithium borohydride; oxalyl dichloride; N,N-diethyl-N-isopropylamine; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(01)00893-0

upstream raw materials:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

Downstream raw materials:

(2S,3S,4S,5R)-1-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecan-5-ol

(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid

(2S,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecan-1-ol

Acetic acid (R)-1-[(1S,2S,3S)-4-hydroxy-2-(4-methoxy-benzyloxy)-1,3-dimethyl-butyl]-tetradecyl ester