(S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 1287228-21-0
• Molecular Formula: C₂₃H₃₃NO₆
• Molecular Weight: 419.518

Synonyms:(S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of (S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

There total 2 articles about (S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 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: 95.0%

(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1287228-20-9) + acetic anhydride (108-24-7) → (S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1287228-21-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1039/c0ob00643b

Reference yield:

(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1287228-19-6) → (S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1287228-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c0ob00643b

Reference yield: 86.0%

(S)-tert-butyl 4-((S,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1287228-21-0) → (4S,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate (1287228-22-1)

Guidance literature:

With iron(III) chloride adsorbed on silica gel; In chloroform; for 12h; Inert atmosphere;

DOI:10.1039/c0ob00643b

upstream raw materials:

(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

acetic anhydride

Downstream raw materials:

(4S,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

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