(2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one

Base Information

• Chemical Name: (2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one
• CAS No.: 865540-23-4
• Molecular Formula: C₂₅H₂₉NO₄S
• Molecular Weight: 439.576
• Mol file: 865540-23-4.mol

Synonyms:(2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one

Chemical Property of (2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one

There total 2 articles about (2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-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: 92.0%

(S)-(-)-2-Benzyloxypent-4-enal (87604-58-8) + (R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one (334968-78-4) → (2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one (865540-23-4)

Guidance literature:

(R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one; With titanium tetrachloride; (-)-sparteine; In dichloromethane; at 0 ℃; for 0.333333h;

(S)-(-)-2-Benzyloxypent-4-enal; With 1-methyl-pyrrolidin-2-one; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ol051543m

Reference yield:

(S)-2-Benzyloxy-pent-4-en-1-ol (69831-69-2) → (2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one (865540-23-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.33 h / 0 °C

2.2: 92 percent / N-methylpyrrolidinone / CH₂Cl₂ / -78 - 0 °C

With oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; (-)-sparteine; In dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/ol051543m

Reference yield: 91.0%

(2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one (865540-23-4) → (2S,3R,4S)-4-Benzyloxy-2-methyl-hept-6-ene-1,3-diol (865540-44-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/ol051543m

upstream raw materials:

(S)-(-)-2-Benzyloxypent-4-enal

(R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one

(S)-2-Benzyloxy-pent-4-en-1-ol

Downstream raw materials:

(2S,3R,4S)-4-Benzyloxy-2-methyl-hept-6-ene-1,3-diol

(2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

[(1R,2S)-2-Benzyloxy-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

2-[(1R,2S)-2-Benzyloxy-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-ethanone