(2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

Base Information

Chemical Name:(2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol
CAS No.:266676-07-7
Molecular Formula:C₃₃H₄₄O₄Si
Molecular Weight:532.795
Hs Code.:

Synonyms:(2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

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Chemical Property of (2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

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Technology Process of (2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

There total 8 articles about (2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-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: 84.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 266676-06-6
(Z)-(2R,3R)-7-(4-Methoxy-benzyloxy)-2,5-dimethyl-hept-4-ene-1,3-diol

: 266676-07-7
(2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1021/ol9904085

Reference yield:

: 266675-80-3
(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

: 266676-07-7
(2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / LiBH₄; MeOH / diethyl ether

2: 84 percent / Et₃N; DMAP / CH₂Cl₂

With methanol; dmap; lithium borohydride; triethylamine; In diethyl ether; dichloromethane; 1: cleavage / 2: silylation;
DOI:10.1021/ol9904085

Reference yield:

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

: 266676-07-7
(2R,3R,Z)-1-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-2,5-dimethylhept-4-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: TfOH / diethyl ether / 20 °C

2.1: nBuLi / tetrahydrofuran / -78 - 20 °C

3.1: tetrahydrofuran / -45 °C

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: MnO₂ / CH₂Cl₂

5.2: 74 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

6.1: 86 percent / LiBH₄; MeOH / diethyl ether

7.1: 84 percent / Et₃N; DMAP / CH₂Cl₂

With methanol; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; trifluorormethanesulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Substitution / 2.1: Substitution / 3.1: Addition / 4.1: Reduction / 5.1: Oxidation / 5.2: Evans aldolization / 6.1: cleavage / 7.1: silylation;
DOI:10.1021/ol9904085