4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one

Base Information

• Chemical Name: 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one
• CAS No.: 623927-76-4
• Molecular Formula: C₂₈H₄₅NO₆Si
• Molecular Weight: 519.754

Synonyms:4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one

Chemical Property of 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one

Chemical Property:

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Technology Process of 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one

There total 3 articles about 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-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:

t-butyldimethylsiyl triflate (69739-34-0) → 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one (623927-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

2: 300 mg / 4-DMAP; Et₃N / CH₂Cl₂ / 7 h / Heating

With 2,6-dimethylpyridine; dmap; triethylamine; In dichloromethane;

DOI:10.1021/ja034841s

Reference yield:

(4R,2'R,3'S,4'S)-3-(2',4'-dimethyl-3',5'-dihydroxyheptanoyl)-4-benzyl-2-oxazolidinone (186489-72-5) → 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one (623927-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

2: 300 mg / 4-DMAP; Et₃N / CH₂Cl₂ / 7 h / Heating

With 2,6-dimethylpyridine; dmap; triethylamine; In dichloromethane;

DOI:10.1021/ja034841s

Reference yield:

propionic acid anhydride (123-62-6) + (R)-4-Benzyl-3-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one (186489-73-6) → 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one (623927-76-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 7h; Heating;

DOI:10.1021/ja034841s

upstream raw materials:

propionic acid anhydride

(R)-4-Benzyl-3-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one

t-butyldimethylsiyl triflate

(4R,2'R,3'S,4'S)-3-(2',4'-dimethyl-3',5'-dihydroxyheptanoyl)-4-benzyl-2-oxazolidinone

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