<3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

Base Information

Chemical Name:<3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene
CAS No.:159517-67-6
Molecular Formula:C₂₃H₃₈O₆Si
Molecular Weight:438.637
Hs Code.:

Synonyms:<3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

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Chemical Property of <3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

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Technology Process of <3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

There total 1 articles about <3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene 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: 94.0%

: 100-39-0
benzyl bromide

: 144901-13-3
<1S-(1α,4β,5α)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol

: 159517-67-6
<3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.7164/antibiotics.47.932

Reference yield: 91.0%

: 159517-67-6
<3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

: 159517-68-7
<3S-(3α,4β,5β)>-5-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.7164/antibiotics.47.932

Reference yield:

: 159517-67-6
<3S-(3α,4β,5β)>-5-Benzyloxy-1-tert-butyldimethylsilyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene

: <1S-(1α,2α,3α,4β,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

2: 49 percent / Ti(O-i-Pr)4, L-DIPT, t-BuOOH / CH₂Cl₂; toluene / 22 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.7164/antibiotics.47.932