(S)-tert-butyl 4-((S,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-((S,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:1287228-19-6
Molecular Formula:C₂₇H₄₅NO₅Si
Molecular Weight:491.744
Hs Code.:

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

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

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

There total 3 articles about (S)-tert-butyl 4-((S,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:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 100-39-0
benzyl bromide

: 151502-81-7
cis-3-dimethyl(1,1-dimethylethyl)silyloxy-1-iodo-1-propene

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

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

With boron trifluoride diethyl etherate; In hexane; toluene; at -95 ℃; for 0.5h; 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:

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

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

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 / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -95 °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:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

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 / 1 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -95 °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