(2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one

Base Information

• Chemical Name: (2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one
• CAS No.: 819799-36-5
• Molecular Formula: C₄₃H₅₃NO₇Si
• Molecular Weight: 723.982
• Mol file: 819799-36-5.mol

Synonyms:(2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one

Chemical Property of (2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one

There total 1 articles about (2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-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: 35.0%

(S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one (496877-70-4) + (2S,3R)-2-benzyloxy-3-(tert-butyldimethylsilanyloxy)-3-phenyl-propionaldehyde (768391-78-2) → (2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one (819799-36-5) + (2'S,3'S,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one (819799-35-4)

Guidance literature:

(S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one; With triethyl borane; trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; at 0 ℃; for 0.5h;

(2S,3R)-2-benzyloxy-3-(tert-butyldimethylsilanyloxy)-3-phenyl-propionaldehyde; In hexane; dichloromethane; at -78 - 0 ℃; for 1.5h;

DOI:10.1039/b411724g

Reference yield: 85.0%

(2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one (819799-36-5) → (2R,3S,4R,5S)-2,4-bis-benzyloxy-3-hydroxy-5-phenyl-tetrahydro-pyran-2-one (819799-43-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1039/b411724g

Reference yield:

(2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bisbenzyloxy-5'-(tert-butyl-dimethyl-silanyloxy)-3'-hydroxy-5'-phenylpentanoyl]-5,5-dimethyl-oxazolidin-2-one (819799-36-5) → (4R,5R)-2,4-bis-benzyloxy-5-phenyl-3,4-dihydro-pyran-2-one

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / TBAF; AcOH / tetrahydrofuran / 16 h / 20 °C

2: 93 percent / DMAP; Et₃N; PhCOCl / CH₂Cl₂ / 18 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; benzoyl chloride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b411724g

upstream raw materials:

(S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one

(2S,3R)-2-benzyloxy-3-(tert-butyldimethylsilanyloxy)-3-phenyl-propionaldehyde

Downstream raw materials:

(2R,3S,4R,5S)-2,4-bis-benzyloxy-3-hydroxy-5-phenyl-tetrahydro-pyran-2-one