(1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

Base Information

Chemical Name:(1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate
CAS No.:146444-28-2
Molecular Formula:C₁₃H₁₄O₄
Molecular Weight:234.252
Hs Code.:

Synonyms:(1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

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Chemical Property of (1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

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Technology Process of (1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

There total 5 articles about (1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate 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: 27.0%

: 146444-26-0
Benzoic acid (1R,2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-yl ester

: 146444-28-2
(1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)88358-7

Reference yield:

: 58564-88-8,113275-48-2,113275-49-3
7-oxa-bicyclo[2.2.1]heptan-2-one

: 146444-28-2
(1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) hexamethyldisilazane, KH / 1) THF, 20 deg C, 2) THF, -78 deg C, 1 h

2: 1) borane, 2) 3 N NaOH, 30percent H₂O₂ / 1) THF, 2) 40 deg C, 30 min

3: 56 percent / Et₃N / CH₂Cl₂ / 20 °C

4: 27 percent / Bu₄NF * 3 H₂O / tetrahydrofuran

With sodium hydroxide; borane; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)88358-7

Reference yield:

: 98-88-4
benzoyl chloride

: 146444-28-2
(1SR,2RS,3SR,4RS)-3-endo-hydroxy-7-oxabicyclo<2.2.1>hept-2-exo-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 27 percent / Bu₄NF * 3 H₂O / tetrahydrofuran

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)88358-7