(S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one
• CAS No.: 1446120-51-9
• Molecular Formula: C₁₈H₂₀INO₄
• Molecular Weight: 441.266
• Mol file: 1446120-51-9.mol

Synonyms:(S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one

There total 1 articles about (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)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: 72.0%

(E)-3-iodo-2-methyl-prop-2-en-1-ol (70396-07-5,149694-62-2,70396-11-1) + (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone (90719-30-5) → (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one (1446120-51-9)

Guidance literature:

(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 2.5h; Molecular sieve; Inert atmosphere;

(E)-3-iodo-2-methyl-prop-2-en-1-ol; In dichloromethane; at -78 - -20 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol401458d

Reference yield: 92.0%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one (1446120-51-9) → (S)-4-benzyl-3-((2S,3S,E)-3-(tert-butyldimethylsilyloxy)-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one (1446120-54-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol401458d

Reference yield:

(S)-4-benzyl-3-((2S,3S,E)-3-hydroxy-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one (1446120-51-9) → C21H33IO4SSi

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 2 h / -78 °C / Inert atmosphere

2: lithium borohydride / tetrahydrofuran; ethanol / 9 h / 0 - 20 °C

3: triethylamine / dichloromethane / 1 h / -10 °C

With 2,6-dimethylpyridine; lithium borohydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ol401458d

upstream raw materials:

(E)-3-iodo-2-methyl-prop-2-en-1-ol

(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone

Downstream raw materials:

(S)-4-benzyl-3-((2S,3S,E)-3-(tert-butyldimethylsilyloxy)-5-iodo-4-methyl-2-vinylpent-4-enoyl)oxazolidin-2-one

(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-{(S,2E,4E)-7-[(2R,3R)-3-{(2R,3S)-3-hydroxypentan-2-yl}oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate