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

Base Information

• Chemical Name: (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 1011247-64-5
• Molecular Formula: C₂₁H₃₁NO₅
• Molecular Weight: 377.481
• Mol file: 1011247-64-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-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: 90.0%

(S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1011247-62-3) → (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1011247-64-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1039/c0ob00643b

Reference yield: 85.0%

(S)-4-[(Z)-(R)-4-(tert-butyldimethylsilanyloxy)-1-hydroxybut-2-enyl]-2',2'-dimethyloxazolidine-3'-carboxylic acid tert-butyl ester (1011247-58-7) + benzyl bromide (100-39-0) → (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1011247-64-5)

Guidance literature:

(S)-4-[(Z)-(R)-4-(tert-butyldimethylsilanyloxy)-1-hydroxybut-2-enyl]-2',2'-dimethyloxazolidine-3'-carboxylic acid tert-butyl ester; benzyl bromide; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; Heating;

With tetrabutyl ammonium fluoride; In dichloromethane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2007.12.014

Reference yield:

(S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-53-4) → (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1011247-64-5)

Guidance literature:

With quinoline; hydrogen; In benzene; at 20 ℃; for 2.75h; Inert atmosphere;

DOI:10.1016/j.tet.2014.02.020

upstream raw materials:

(S)-4-[(Z)-(R)-4-(tert-butyldimethylsilanyloxy)-1-hydroxybut-2-enyl]-2',2'-dimethyloxazolidine-3'-carboxylic acid tert-butyl ester

benzyl bromide

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

C₂₇H₄₃NO₅Si

Downstream raw materials:

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

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

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

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