(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
CAS No.:196503-54-5
Molecular Formula:C₁₆H₁₇NO₅S
Molecular Weight:335.381
Hs Code.:

Synonyms:(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

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Chemical Property of (1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

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Technology Process of (1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

There total 5 articles about (1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 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: 71.0%

: 67-56-1
methanol

: (1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

: 196503-54-5
(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Guidance literature:: With tetrachloromethane; triphenylphosphine; for 18h; Ambient temperature;
DOI:10.1055/s-1997-942

Reference yield:

: 70190-87-3
(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid

: 196503-54-5
(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85.4 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2: 91.2 percent / Et₃N, propylphosphonic anhydride, NH₃ / CH₂Cl₂ / 0.08 h / 0 °C

3: 93.8 percent / Oxon^R₈ / methanol; H₂O / 2 h / Ambient temperature

4: 1.) Ph₂Se₂, Na, 2.) <18>crown-6 / 24 h / Ambient temperature; 1.) THF, parrafin oil; 2.) THF

5: Ph₃P / CCl₄ / 18 h / Ambient temperature

With 18-crown-6 ether; Oxon^R₈; diphenyl diselenide; propylphosphonic anhydride; ammonia; sodium; triethylamine; triphenylphosphine; In methanol; tetrachloromethane; dichloromethane; water;
DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T

Reference yield:

: 196503-52-3
(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide

: 196503-54-5
(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 93.8 percent / Oxon^R₈ / methanol; H₂O / 2 h / Ambient temperature

2: 1.) Ph₂Se₂, Na, 2.) <18>crown-6 / 24 h / Ambient temperature; 1.) THF, parrafin oil; 2.) THF

3: Ph₃P / CCl₄ / 18 h / Ambient temperature

With 18-crown-6 ether; Oxon^R₈; diphenyl diselenide; sodium; triphenylphosphine; In methanol; tetrachloromethane; water;
DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T