(1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

Base Information

Chemical Name:(1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate
CAS No.:146352-44-5
Molecular Formula:C₁₃H₁₀Cl₂O₄
Molecular Weight:301.126
Hs Code.:

Synonyms:(1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

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Chemical Property of (1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

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Technology Process of (1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

There total 6 articles about (1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate 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: 13.2%

: 128503-25-3
(+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate

: 128503-26-4
(1S,2S,3S,4S,5S)-5-endo-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

: 146352-44-5
(1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

Guidance literature:: With hydrogen; sodium carbonate; palladium on activated charcoal; In ethyl acetate; under 760 Torr; a) 15 h, b) 20 deg C, 24 h;
DOI:10.1016/S0040-4020(01)88357-5

Reference yield:

: 128503-25-3,146388-99-0
(+/-)-(1RS,2RS,3SR,4SR)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate

: 146352-44-5,146389-01-7
(1RS,3RS,4RS,5RS)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

: 128503-26-4,146389-00-6
(1RS,2RS,3RS,4RS,5RS)-5-endo-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

Guidance literature:: With hydrogen; sodium carbonate; palladium on activated charcoal; In ethyl acetate; under 760 Torr; a) 15 h, b) 20 deg C, 24 h;
DOI:10.1016/S0040-4020(01)88357-5

Reference yield:

: 88708-22-9
(+)-(1R,4R)-7-oxabicyclo<2.2.1>-hept-5-en-2-one

: 146352-44-5
(1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

Guidance literature:: Multi-step reaction with 4 steps

2: 95 percent / Et₃N / dimethylformamide / 40 °C

3: 69 percent / AcONa / CH₂Cl₂ / a) 0 deg C, 5 min., b) 20 deg C, 30 min.

4: 13.2 percent / Na₂CO₃, H₂ / 10percent Pd/C / ethyl acetate / 760 Torr / a) 15 h, b) 20 deg C, 24 h

With hydrogen; sodium acetate; sodium carbonate; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)88357-5