(2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Base Information

Chemical Name:(2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
CAS No.:220724-82-3
Molecular Formula:C₂₇H₄₀N₂O₈
Molecular Weight:520.623
Hs Code.:

Synonyms:(2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

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Chemical Property of (2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

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Technology Process of (2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

There total 7 articles about (2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl 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%

: 501-53-1,94274-21-2
benzyl chloroformate

: (2S,5S)-5-[(tert-Butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

: 220724-82-3
(2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Guidance literature:: With 4-methyl-morpholine; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/S0960-894X(98)00550-2

Reference yield:

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

: 220724-82-3
(2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / DMAP, Et₃N

2: p-TsOH

3: BF₃*OEt₂, CuBr*SMe₂ / diethyl ether; tetrahydrofuran / -78 °C

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

5: 90 percent / NaBH₃CN / methanol / 0 - 20 °C

6: 90 percent / NMM / tetrahydrofuran / -78 - 20 °C

With 4-methyl-morpholine; dmap; copper(I) bromide dimethylsulfide complex; dimethylsulfide; boron trifluoride diethyl etherate; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1016/S0960-894X(98)00550-2

Reference yield:

: 144978-35-8,144978-12-1,251924-83-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate

: 220724-82-3
(2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH

2: BF₃*OEt₂, CuBr*SMe₂ / diethyl ether; tetrahydrofuran / -78 °C

3: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

4: 90 percent / NaBH₃CN / methanol / 0 - 20 °C

5: 90 percent / NMM / tetrahydrofuran / -78 - 20 °C

With 4-methyl-morpholine; copper(I) bromide dimethylsulfide complex; dimethylsulfide; boron trifluoride diethyl etherate; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1016/S0960-894X(98)00550-2