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

Base Information

Chemical Name:<1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane
CAS No.:159517-65-4
Molecular Formula:C₁₇H₂₄O₇
Molecular Weight:340.373
Hs Code.:

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

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Chemical Property of <1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

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Technology Process of <1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

There total 4 articles about <1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane 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: 49.0%

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

: 159517-65-4
<1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

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

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In dichloromethane; toluene; for 22h; Ambient temperature;
DOI:10.7164/antibiotics.47.932

Reference yield:

: 100-39-0
benzyl bromide

: 159517-65-4
<1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / NaH / dimethylformamide / 2 h / 0 °C

2: 91 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

3: 24 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; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.7164/antibiotics.47.932

Reference yield:

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

: 159517-65-4
<1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / NaH / dimethylformamide / 2 h / 0 °C

2: 91 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

3: 24 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; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.7164/antibiotics.47.932