8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

Base Information

Chemical Name:8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate
CAS No.:433713-64-5
Molecular Formula:C₂₃H₂₆O₆
Molecular Weight:398.456
Hs Code.:

Synonyms:8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

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Chemical Property of 8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

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Technology Process of 8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

There total 4 articles about 8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate 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%

: 2386-64-3
ethylmagnesium chloride

: 433713-58-7
[8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]octane]-(2-oxo-2-phenyl)-ethanoate

: 433713-64-5
8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

Guidance literature:: With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 20 ℃;
DOI:10.1016/S0040-4020(02)00024-8

Reference yield:

: 100-39-0
benzyl bromide

: 433713-64-5
8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 40 percent / potassium hydroxide / H₂O / Heating

2: 95 percent / para-toluenesulfonic acid / toluene / 24 h / Heating

3: 65 percent / zinc chloride / diethyl ether; tetrahydrofuran / 20 °C

With potassium hydroxide; toluene-4-sulfonic acid; zinc(II) chloride; In tetrahydrofuran; diethyl ether; water; toluene;
DOI:10.1016/S0040-4020(02)00024-8

Reference yield:

: 111956-66-2
(3R,3aR,6S,6aR)-6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol

: 433713-64-5
8-(1R,4S,5R,8R)-4-benzyloxy-2,6-dioxabicyclo[3.3.0]-(2-hydroxy-2-phenyl)-butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / para-toluenesulfonic acid / toluene / 24 h / Heating

2: 65 percent / zinc chloride / diethyl ether; tetrahydrofuran / 20 °C

With toluene-4-sulfonic acid; zinc(II) chloride; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4020(02)00024-8