(S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one
• CAS No.: 1439376-72-3
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 1439376-72-3.mol

Synonyms:(S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one

There total 8 articles about (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)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:

(2S,4R,5R)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-5-hydroxy-2,4-dimethyloct-6-yne-1,3-dione (1439376-49-4) → (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-72-3) + (S)-4-benzyl-3-((2S)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -50 - 10 ℃; Inert atmosphere;

DOI:10.1002/anie.201206670

Reference yield:

(2S,4R,5R)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-5-hydroxy-2,4-dimethyloct-6-yne-1,3-dione (1439376-49-4) → (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-72-3) + C20H25NO5

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -50 - 10 ℃; Overall yield = 98 %; Overall yield = 1 g; Inert atmosphere;

DOI:10.1021/ja508846g

Reference yield:

(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0) → (S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; tin(II) trifluoromethanesulfonate / diethyl ether / -78 °C / Inert atmosphere

1.2: 1.5 h / 0 °C / Inert atmosphere

2.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -50 - 10 °C / Inert atmosphere

With tin(II) trifluoromethanesulfonate; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In diethyl ether; acetonitrile;

DOI:10.1021/ja508846g

upstream raw materials:

(4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone

(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione

(2S,4R,5R)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-5-hydroxy-2,4-dimethyloct-6-yne-1,3-dione

(S)-4-benzyl-3-propionyl-2-oxazolidinone

Downstream raw materials:

(S)-4-benzyl-3-((2S,3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one