(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

Base Information

Chemical Name:(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol
CAS No.:345342-57-6
Molecular Formula:C₂₁H₂₄O₅
Molecular Weight:356.419
Hs Code.:

Synonyms:(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

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Chemical Property of (1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

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Technology Process of (1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

There total 8 articles about (1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-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: 95.0%

: 345342-63-4
Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

: 345342-57-6
(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

Guidance literature:: With sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

: 79549-73-8
benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

: 345342-57-6
(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / NaH / dimethylformamide

2.1: 86 percent / NaBH₃CN; HCl / diethyl ether; tetrahydrofuran

3.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂

4.1: 66 percent / diethyl ether

5.1: 100 percent / p-TsOH / Pd/C / methanol; H₂O

6.1: Bu₂SnO / benzene

6.2: 91 percent / Et₃N / dioxane

7.1: 94 percent / i-Pr₂NEt / CH₂Cl₂

8.1: 95 percent / NaH / tetrahydrofuran; methanol

With hydrogenchloride; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 3.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

: 345342-55-4
(2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

: 345342-57-6
(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 66 percent / diethyl ether

2.1: 100 percent / p-TsOH / Pd/C / methanol; H₂O

3.1: Bu₂SnO / benzene

3.2: 91 percent / Et₃N / dioxane

4.1: 94 percent / i-Pr₂NEt / CH₂Cl₂

5.1: 95 percent / NaH / tetrahydrofuran; methanol

With sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/S0040-4039(01)00355-0