(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

Base Information

Chemical Name:(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol
CAS No.:423118-46-1
Molecular Formula:C₃₄H₄₆O₄Si
Molecular Weight:546.822
Hs Code.:

Synonyms:(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

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Chemical Property of (2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

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Technology Process of (2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

There total 10 articles about (2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-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: 62.0%

: 423118-38-1
(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-2-methylhept-6-ene-1,3-diol

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 423118-46-1
(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃; for 72h;
DOI:10.1039/b507570j

Reference yield: 42.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 423117-83-3
(2'S,3'R,4R,5S,5'R)-3-{5'-[2''-(tert-butyldiphenylsilanyloxy)-ethyl]-3'-hydroxy-2'-methylhept-6'-enoyl}-4-methyl-5-phenyloxazolidin-2-one

: 423118-46-1
(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

Guidance literature:: (2'S,3'R,4R,5S,5'R)-3-{5'-[2''-(tert-butyldiphenylsilanyloxy)-ethyl]-3'-hydroxy-2'-methylhept-6'-enoyl}-4-methyl-5-phenyloxazolidin-2-one; With lithium borohydride; In methanol; diethyl ether; at 0 ℃; for 2h;

O-(4-methoxybenzyl)-trichloroacetimidate; With camphor-10-sulfonic acid; In dichloromethane; at -20 - 0 ℃; for 72h;
DOI:10.1016/S0040-4039(01)02154-2

Reference yield:

: 256494-25-4
(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate

: 423118-46-1
(2R,3R,5S)-5-[2'-(tert-butyldiphenylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -78 °C

2.1: 78 percent / Hg(O₂CCF₃)2 / 8 h / 20 °C

3.1: 97 percent / toluene / 36 h / 170 °C

4.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -78 °C

4.2: 39 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: 96 percent / LiBH₄ / methanol; diethyl ether / 2.5 h / 0 - 20 °C

6.1: 62 percent / camphorsulfonic acid / CH₂Cl₂ / 72 h / 0 °C

With lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; mercury(II) trifluoroacetate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; toluene; 3.1: Claisen rearrangement / 4.2: Evans aldol reaction;
DOI:10.1039/b507570j