2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:865436-10-8
Molecular Formula:C₄₆H₆₃N₅O₁₂S
Molecular Weight:910.099
Hs Code.:

2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

Synonyms:2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of 2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of 2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

There total 5 articles about 2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl 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: 48.0%

: 865436-09-5
2S,4R-4-carboxymethoxy-2-(pyridin-2-ylaminomethyl)pyrrolidine-1-carboxylic acid benzyl ester

: 24424-99-5
di-tert-butyl dicarbonate

: 185563-98-8
3S-3-amino-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid tert-butyl ester

: 865436-10-8
2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: 2S,4R-4-carboxymethoxy-2-(pyridin-2-ylaminomethyl)pyrrolidine-1-carboxylic acid benzyl ester; 3S-3-amino-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid tert-butyl ester; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); for 2.5h;

di-tert-butyl dicarbonate; With dmap; In tetrahydrofuran; at 20 ℃; for 120h;

Reference yield:

: C₃₆H₄₇N₅O₈S

: 24424-99-5
di-tert-butyl dicarbonate

: 865436-10-8
2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With dmap; In tetrahydrofuran; at 20 ℃; for 120h;
DOI:10.1021/jm070002v

Reference yield:

: 773-64-8
2-mesitylenesulphonyl chloride

: 865436-10-8
2S,3R,5S-4-(2-{[2-tert-butoxycarbonyl-2-(2,4,6-trimethylbenzenesulfonyl-tert-butoxycarbonylamino)-2-(tert-butoxycarbonyl)ethyl]amino}-2-oxoethoxy)-2-[(tert-butoxycarbonylpyridin-2-ylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NEt₃ / tetrahydrofuran; H₂O

2.1: NaOH; Br₂ / H₂O

2.2: H₂SO₄ / dioxane

3.1: O-benzotriazole-N,N,N',N'-tetramethyluronium*PF₆; diisopropylethylamine / dimethylformamide / 2.5 h

4.1: 3.11 g / DMAP / tetrahydrofuran / 120 h / 20 °C

With dmap; sodium hydroxide; bromine; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; 2.1: Hofmann rearrangement;
DOI:10.1021/jm070002v