<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

Base Information

Chemical Name:<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol
CAS No.:160343-91-9
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

Synonyms:<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

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Chemical Property of <1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

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Technology Process of <1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

There total 13 articles about <1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-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: 99.0%

: 160343-90-8
<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>-6-oxabicyclo<3.1.0>hexane

: 160343-91-9
<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1016/S0040-4039(00)75990-9

Reference yield: 65.0%

: 89291-76-9
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

: 160343-91-9
<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

: 247909-16-6
(4aR)-4,4a-Anhydro-5-O-benzyl-4a-carba-2,3-O-isopropylidene-β-D-ribofuranose

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 12h;
DOI:10.1515/znb-1999-0816

Reference yield:

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

: 160343-91-9
<1R-(1α,2α,3α,4α,5α)>-1-<(Benzyloxy)methyl>-2,3-(isopropylidenedioxy)-6-oxabicyclo<3.1.0>hexan-4-ol

Guidance literature:: Multi-step reaction with 10 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: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

7: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: 100 percent / NaH / dimethylformamide; paraffin / 2 h / Ambient temperature

9: 55 percent / 85percent MCPBA / CHCl₃ / 24 h / Ambient temperature

10: 99 percent / DDQ, H₂O / CH₂Cl₂ / 3 h / 24 °C

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; pyridinium p-toluenesulfonate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021