3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester
• CAS No.: 646532-29-8
• Molecular Formula: C₄₄H₆₁N₅O₁₄
• Molecular Weight: 883.993
• Mol file: 646532-29-8.mol

Synonyms:3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester

Chemical Property of 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester

There total 5 articles about 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-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: 44.0%

(2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester (646532-92-5) + Cbz-Leu-Glu(O-t-Bu)-Thr-NHNHCH2COO-t-Bu (646532-81-2) → 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester (646532-29-8)

Guidance literature:

(2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester; With 4-methyl-morpholine; isobutyl chloroformate; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

Cbz-Leu-Glu(O-t-Bu)-Thr-NHNHCH₂COO-t-Bu; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jm0305016

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester (646532-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 34 percent / 4-methylmorpholine / dimethylformamide / 20.5 h / -10 - 20 °C

2.1: N-methylmorpholine; isobutyl chloroformate / dimethylformamide / 0.5 h / 0 °C

2.2: 44 percent / dimethylformamide / 0 - 20 °C

With 4-methyl-morpholine; isobutyl chloroformate; In N,N-dimethyl-formamide;

DOI:10.1021/jm0305016

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 3-(N'-{2-[2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-hydroxy-butyryl}-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl)-oxirane-2-carboxylic acid benzyl ester (646532-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-(dimethylamino)pyridine / dimethylformamide / 15 h / 20 °C

2.1: N-methylmorpholine; isobutyl chloroformate / dimethylformamide / 0.5 h / 0 °C

2.2: 44 percent / dimethylformamide / 0 - 20 °C

With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; isobutyl chloroformate; In N,N-dimethyl-formamide;

DOI:10.1021/jm0305016

upstream raw materials:

(2S,3S)-oxirane-2,3-dicarboxylic acid monobenzyl ester

Cbz-Leu-Glu(O-t-Bu)-Thr-NHNHCH₂COO-t-Bu

bromoacetic acid tert-butyl ester

benzyl alcohol