Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, phenylmethyl ester, (1R,2S,3R,4S)-

Base Information

Chemical Name:Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, phenylmethyl ester, (1R,2S,3R,4S)-
CAS No.:660439-21-4
Molecular Formula:C29H33NO5
Molecular Weight:475.585
Hs Code.:

Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid,
3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carb
onyl]-, phenylmethyl ester, (1R,2S,3R,4S)-

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Chemical Property of Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, phenylmethyl ester, (1R,2S,3R,4S)-

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Technology Process of Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, phenylmethyl ester, (1R,2S,3R,4S)-

There total 1 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carb onyl]-, phenylmethyl ester, (1R,2S,3R,4S)- 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: 85.0%

: 16874-17-2
L-phenylalanine tert-butyl ester

: 581100-26-7
(2R,3S)-3-endo-benzyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

: 660439-21-4
(2S,3R)-3-endo-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid benzyl ester

Guidance literature:: With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 13h;
DOI:10.1021/jo030295+

Reference yield: 99.0%

: 660439-21-4
(2S,3R)-3-endo-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid benzyl ester

: 660439-25-8
(2S,3R)-3-endo-(1-(tert-butoxycarbonyl)-2-phenyl-ethylcarbamoyl)bicyclo[2.2.1]heptane-2-endo-carboxylic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate;
DOI:10.1021/jo030295+

Reference yield:

: 660439-21-4
(2S,3R)-3-endo-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid benzyl ester

: (2S,3R)-2-{[3-endo-(1-(tert-butoxycarbonyl)-2-phenylethylcarbamoyl)bicyclo[2.2.1]heptane-2-endo-carbonyl]amino}-3-phenylpropionic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / H₂ / Pd/C / ethyl acetate

2: 91 percent / DCC; HOBt; DMAP / CH₂Cl₂ / 13 h / 0 - 20 °C

With dmap; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1021/jo030295+