tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

Base Information

Chemical Name:tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate
CAS No.:1429183-70-9
Molecular Formula:C₂₉H₄₁NO₄Si
Molecular Weight:495.734
Hs Code.:

Synonyms:tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

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Chemical Property of tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

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Technology Process of tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

There total 7 articles about tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-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: 56.0%

: 1315158-32-7
tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate

: 106-95-6
allyl bromide

: 1429183-69-6
tert-butyl (3R,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

: 1429183-70-9
tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

Guidance literature:: With ammonium chloride; zinc; In tetrahydrofuran; water; at 20 ℃; for 6h; Overall yield = 93 %; stereoselective reaction;
DOI:10.1055/s-0032-1317962

Reference yield: 56.0%

: 1315158-32-7
tert-butyl (2R,3R)-3-(tert-butyldiphenylsilyloxy)-1-oxopent-4-en-2-ylcarbamate

: 1730-25-2
allylmagnesium bromide

: 1429183-69-6
tert-butyl (3R,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

: 1429183-70-9
tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 - -30 ℃; stereoselective reaction;
DOI:10.1055/s-0032-1317962

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1429183-70-9
tert-butyl (3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxyocta-1,7-dien-4-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1: 1H-imidazole / dichloromethane / 4 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

4: tetrahydrofuran; diethyl ether / -78 - -30 °C

With 1H-imidazole; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1055/s-0032-1317962