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

Base Information

• Chemical Name: (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 1011247-62-3
• Molecular Formula: C₂₇H₄₅NO₅Si
• Molecular Weight: 491.744
• Mol file: 1011247-62-3.mol

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

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

There total 5 articles about (S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)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:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) + benzyl bromide (100-39-0) + cis-3-dimethyl(1,1-dimethylethyl)silyloxy-1-iodo-1-propene (151502-81-7) → (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)

Guidance literature:

cis-3-dimethyl(1,1-dimethylethyl)silyloxy-1-iodo-1-propene; With n-butyllithium; In hexane; toluene; at -78 ℃; for 0.75h; Inert atmosphere;

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In hexane; toluene; at -78 ℃; for 0.75h; Inert atmosphere;

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; benzyl bromide; stereoselective reaction; Further stages;

DOI:10.1039/c0ob00643b

Reference yield:

tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium; iodine / tetrahydrofuran / -78 °C / Inert atmosphere

2.1: dipotassium (E)-diazene-1,2-dicarboxylate; acetic acid / methanol / Inert atmosphere

3.1: n-butyllithium / hexane; toluene / 0.75 h / -78 °C / Inert atmosphere

3.2: 0.75 h / -78 °C / Inert atmosphere

With n-butyllithium; dipotassium (E)-diazene-1,2-dicarboxylate; iodine; acetic acid; In tetrahydrofuran; methanol; hexane; toluene;

DOI:10.1039/c0ob00643b

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium; iodine / tetrahydrofuran / -78 °C / Inert atmosphere

3.1: dipotassium (E)-diazene-1,2-dicarboxylate; acetic acid / methanol / Inert atmosphere

4.1: n-butyllithium / hexane; toluene / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.75 h / -78 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; dipotassium (E)-diazene-1,2-dicarboxylate; iodine; acetic acid; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c0ob00643b

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

tert-Butyldimethyl(prop-2-ynyloxy)silane

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

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

(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