(1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Base Information

Chemical Name:(1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol
CAS No.:110115-27-0
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

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

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Chemical Property of (1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

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Technology Process of (1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

There total 4 articles about (1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-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:

: 89731-34-0
1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-hydroxypropynyl)-β-D-glucopyranose

: 110115-27-0
(1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: With hydrogen; Lindlar catalyst; In ethyl acetate;
DOI:10.1021/jo00229a013

Reference yield:

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

: 110115-27-0
(1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi, 2.) Et₂AlCl

2: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

3: H₂ / 5percent Pd/CaCO₃, lead oxide / ethyl acetate

With n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; diethylaluminium chloride; Lindlar catalyst; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jo00229a013

Reference yield:

: 110046-81-6
1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose

: 110115-27-0
(1R,2S,3R,4R,5R)-2-Benzyloxy-4-((Z)-3-hydroxy-propenyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2: H₂ / 5percent Pd/CaCO₃, lead oxide / ethyl acetate

With tetrabutyl ammonium fluoride; hydrogen; Lindlar catalyst; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jo00229a013