(S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester

Base Information

• Chemical Name: (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester
• CAS No.: 83704-69-2
• Molecular Formula: C₃₁H₃₉N₃O₈
• Molecular Weight: 581.666

Synonyms:(S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester

Chemical Property of (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester

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Technology Process of (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester

There total 2 articles about (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic 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: 100.0%

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid (5680-86-4) + (S)-prolylglycine t-butyl ester (71666-99-4) → (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester (83704-69-2)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide;

DOI:10.1021/ja00388a114

Reference yield:

Z-Pro-Gly-OBut (5617-01-6) → (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester (83704-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / aq. ethanol

2: 100 percent / DCC/HOBt

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol;

DOI:10.1021/ja00388a114

Reference yield:

(S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester (83704-69-2) → (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid; hydrochloride

Guidance literature:

With hydrogenchloride; hydrogen; In ethanol;

DOI:10.1021/ja00388a114

upstream raw materials:

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

(S)-prolylglycine t-butyl ester

Z-Pro-Gly-OBu^t

Downstream raw materials:

({(S)-1-[(S)-2-Amino-4-((S)-1-{(S)-1-[(S)-2-(N'-benzyloxycarbonyl-hydrazino)-1-methyl-2-oxo-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-butyryl]-pyrrolidine-2-carbonyl}-amino)-acetic acid tert-butyl ester

phthalyl-Glu(Leu-Phe-Ala-NHNHZ)-Pro-Gly-O-t-Bu

Boc-Pro-Gly-Glu(Leu-Phe-Ala-NHNHZ)-Pro-Gly-O-t-Bu

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