(2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

Base Information

Chemical Name:(2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol
CAS No.:88392-90-9
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:(2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

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Chemical Property of (2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

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Technology Process of (2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

There total 6 articles about (2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-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: 65.0%

: 88412-19-5
(2S,3R,4R)-2-Benzyloxy-4-[(Z)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propenyl]-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

: 88392-90-9
(2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

Guidance literature:: solvolysis;
DOI:10.1021/ja00315a046

Reference yield:

: 33208-47-8
4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

: 88392-90-9
(2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) magnesium turnings, ethylene bromide / 1.) ether, hexane, RT, 1 h, 2.) ether, hexane, RT, 4 h

2: tetra-n-butylammonim fluoride / tetrahydrofuran / 0.5 h / 0 °C

3: CF₃COOH, Et₃N / 0.08 h / var. solvents, temperatures and catalysts

With tetrabutyl ammonium fluoride; magnesium; ethylene dibromide; triethylamine; trifluoroacetic acid; In tetrahydrofuran;
DOI:10.1021/jo00229a013

Reference yield:

: 110046-94-1
(1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-methoxymethoxy-2-methyl-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

: 88392-90-9
(2R,3S,4R,4aR,8aS)-3-Benzyloxy-2-hydroxymethyl-6-methyl-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: HCl / diethyl ether / 20 h

2: CF₃COOH, Et₃N / 0.08 h / var. solvents, temperatures and catalysts

With hydrogenchloride; triethylamine; trifluoroacetic acid; In diethyl ether;
DOI:10.1021/jo00229a013