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

Base Information

Chemical Name:<1R-(1α,2α,3β,4α,5α)>-2-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane
CAS No.:144811-27-8
Molecular Formula:C₁₇H₂₄O₇
Molecular Weight:340.373
Hs Code.:

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

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

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

There total 12 articles about <1R-(1α,2α,3β,4α,5α)>-2-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(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: 94.0%

: 144811-26-7
<3S-(3α,4β,5α)>-5-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-1-cyclopentene

: 144811-27-8
<1R-(1α,2α,3β,4α,5α)>-2-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 5h;
DOI:10.1021/ja00051a051

Reference yield:

: 144811-22-3
(4S-trans)-2-(Hydroxymethyl)-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one

: 144811-27-8
<1R-(1α,2α,3β,4α,5α)>-2-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / imidazole / dimethylformamide / 1.) 0 deg C, 10 min, 2.) 25 deg C, 16 h

2: 53 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1.) 0 deg C, 30 min, 2.) 25 deg C, 2 h

3: 75 percent / NaH / dimethylformamide / 1 h / 0 °C

4: TBAF / tetrahydrofuran / 1 h / 0 °C

5: 94 percent / Ti(O-i-Pr)4, t-BuOOH, diisopropyl L-tartrate / CH₂Cl₂; toluene / 5 h / -25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00083a023

Reference yield:

: 144811-23-4
(4S-trans)-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one

: 144811-27-8
<1R-(1α,2α,3β,4α,5α)>-2-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 4 steps

1: 53 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1.) 0 deg C, 30 min, 2.) 25 deg C, 2 h

2: 75 percent / NaH / dimethylformamide / 1 h / 0 °C

3: TBAF / tetrahydrofuran / 1 h / 0 °C

4: 94 percent / Ti(O-i-Pr)4, t-BuOOH, diisopropyl L-tartrate / CH₂Cl₂; toluene / 5 h / -25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00083a023