tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

Base Information

Chemical Name:tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate
CAS No.:1345017-46-0
Molecular Formula:C₃₃H₄₃NO₄Si
Molecular Weight:545.794
Hs Code.:

Synonyms:tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

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Chemical Property of tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

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Technology Process of tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

There total 5 articles about tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate 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: 70.0%

: 1345017-45-9
tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate

: 1345017-46-0
tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

Guidance literature:: tert-butyl (2S,3R)-3-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; hexane; water; at 0 ℃; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

: 1042339-01-4
(1S,2R)-(2-benzyloxy-1-hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester

: 1345017-46-0
tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; 2.1: Wittig rearrangement;
DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

: 114301-34-7,114301-35-8,117487-60-2,122709-37-9,117487-58-8
tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1345017-46-0
tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-6-phenylhex-3-en-2-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: acetic acid / methanol; water / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; sodium hydride; acetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 4.1: Wittig rearrangement;
DOI:10.1016/j.tetlet.2011.08.084