(4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

Base Information

Chemical Name:(4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol
CAS No.:1374036-52-8
Molecular Formula:C₃₂H₄₂O₄Si
Molecular Weight:518.769
Hs Code.:

Synonyms:(4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

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Chemical Property of (4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

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Technology Process of (4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

There total 14 articles about (4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-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: 89.0%

: 854749-30-7
(S)-5-((tert-butyldiphenylsilyl)oxy)-3-((4-methoxybenzyl)oxy)pentanal

: 1730-25-2
allylmagnesium bromide

: 1374036-52-8
(4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

Guidance literature:: allylmagnesium bromide; With (+)-B-methoxydiisocamphenylborane; In diethyl ether; at 0 - 20 ℃; for 1.5h;

(S)-5-((tert-butyldiphenylsilyl)oxy)-3-((4-methoxybenzyl)oxy)pentanal; In diethyl ether; at -78 - 20 ℃; for 17h; stereoselective reaction;
DOI:10.1021/ol500996n

Reference yield: 82.0%

: 1374036-51-7
tert.-butyl((S)-3-(4-methoxybenzyloxy)-4-((S)-oxiran-2-yl)butoxy)diphenylsilane

: 1826-67-1
vinyl magnesium bromide

: 1374036-52-8
(4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

Guidance literature:: vinyl magnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -20 ℃; for 0.25h;

tert.-butyl((S)-3-(4-methoxybenzyloxy)-4-((S)-oxiran-2-yl)butoxy)diphenylsilane; In tetrahydrofuran; at -40 ℃; for 0.5h;
DOI:10.1039/c2ob25151e

Reference yield:

: 633305-66-5
(R)-tert-butyl-(3-(4-methoxybenzyloxy)hex-5-enyloxy)-diphenylsilane

: 1374036-52-8
(4R,6S)-8-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-oct-1-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; acetone; water / 2 h / 20 °C

1.2: 0.5 h / 20 °C

2.1: (+)-B-methoxydiisocamphenylborane / diethyl ether / 1.5 h / 0 - 20 °C

2.2: 17 h / -78 - 20 °C

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; water; acetone;
DOI:10.1021/ol500996n