(3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

Base Information

Chemical Name:(3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol
CAS No.:912805-57-3
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

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Chemical Property of (3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

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Technology Process of (3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

There total 6 articles about (3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol 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: 67.0%

: 124010-06-6
(R)-(+)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentanal

: 590-18-1
(Z)-2-Butene

: 912805-57-3
(3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

Guidance literature:: (Z)-2-Butene; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 - -25 ℃; Inert atmosphere;

With boron trifluoride diethyl etherate; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; hexane; at -78 - -25 ℃;

(R)-(+)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentanal; Further stages;
DOI:10.1055/s-0030-1257890

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 912805-57-3
(3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran

1.2: 70 percent / n-BuLi

2.1: 100 percent / hydrogen / Ru₂Cl₂[(R)-BINAP]2*Et₃N / methanol / 66 h / 23 °C / 42923.3 Torr

3.1: 99 percent / imidazole / dimethylformamide / 15 h / 23 °C

4.1: 93 percent / DIBAL-H / petroleum ether; toluene / 0.08 h / -78 °C

5.1: n-butyllithium; potassium tert-butoxide / petroleum ether; tetrahydrofuran / -78 - -45 °C

5.2: boron trifluoride diethyl etherate / (+)-B-methoxydiisopinocamphenylborane / petroleum ether; tetrahydrofuran; diethyl ether / -78 °C

5.3: petroleum ether; tetrahydrofuran; diethyl ether / 8.5 h

With 1H-imidazole; n-butyllithium; potassium tert-butylate; hydrogen; sodium hydride; diisobutylaluminium hydride; Ru₂Cl₂[(R)-BINAP]2*Et₃N; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; Petroleum ether;
DOI:10.1021/ja062364i

Reference yield:

: 124010-06-6
(R)-(+)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentanal

: 590-18-1
(Z)-2-Butene

: 912805-57-3
(3S,4S,6R)-(-)-8-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-3-methyloct-1-en-4-ol

: 8-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-1-en-4-ol

Guidance literature:: (Z)-2-Butene; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; Petroleum ether; at -78 - -45 ℃;

With boron trifluoride diethyl etherate; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; Petroleum ether; at -78 ℃;

(R)-(+)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentanal; In tetrahydrofuran; diethyl ether; Petroleum ether; for 8.5h;
DOI:10.1021/ja062364i