(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Base Information

Chemical Name:(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester
CAS No.:372187-25-2
Molecular Formula:C₃₁H₅₀N₂O₈Si
Molecular Weight:606.832
Hs Code.:

(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Synonyms:(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

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Chemical Property of (2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

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Technology Process of (2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

There total 12 articles about (2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-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: 90.0%

: 372187-46-7
5-allyl-2-[2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

: 372187-25-2
(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; diethyl ether; at -50 - 10 ℃;
DOI:10.1021/ja016403w

Reference yield: 85.0%

: 372187-46-7
5-allyl-2-[2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionyl]-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

: 372187-24-1
(2R,5R)-5-allyl-2-[(1R,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

: 372187-25-2
(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; diethyl ether; at -50 - 0 ℃; for 1h;
DOI:10.1016/j.tet.2010.12.068

Reference yield:

: 372187-43-4
(2R,5R)-5-Allyl-2-[(R)-((R)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-hydroxy-methyl]-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

: 372187-25-2
(2R,5R)-5-allyl-2-[(1S,2R)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyl-oxy)-1-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / CSA / methanol / 7 h / 0 °C

2: 97 percent / triethylamine; DMAP / CH₂Cl₂ / -50 - 0 °C

3: 95 percent / oxalic chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -50 - 0 °C

4: 90 percent / NaBH₄ / methanol; diethyl ether / -50 - 10 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; 3: Swern oxidation;
DOI:10.1021/ja016403w