<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

Base Information

Chemical Name:<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane
CAS No.:160343-81-7
Molecular Formula:C₂₃H₃₄O₇Si
Molecular Weight:450.604
Hs Code.:

Synonyms:<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

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Chemical Property of <1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

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Technology Process of <1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

There total 7 articles about <1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-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: 89.0%

: 160343-80-6
<1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene

: 160343-81-7
<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 24 ℃; for 96h;
DOI:10.1016/S0040-4039(00)75990-9

Reference yield:

: 5336-08-3
D-Ribono-1,4-lactone

: 160343-81-7
<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 7 steps

1: 2.) 1 M aq. HCl / 1.) pyridinium p-toluenesulfonate / 1.) 50 deg C, 1 h, 2.) THF, 24 - 25 deg C, 1 h

2: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 43 percent / DABCO / dimethylformamide / 1 h

5: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

6: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

7: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; dmap; sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; pyridinium p-toluenesulfonate; In ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00095a021

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 160343-81-7
<1R-(1α,2α,3α,4α,5α)>-4-<(Benzyloxycarbonyl)oxy>-1-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 43 percent / DABCO / dimethylformamide / 1 h

4: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

5: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

6: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00095a021