(S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester
• CAS No.: 726192-26-3
• Molecular Formula: C₁₈H₂₆N₂O₆
• Molecular Weight: 366.414

Synonyms:(S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester

Chemical Property of (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester

Chemical Property:

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Technology Process of (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester

There total 2 articles about (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric 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: 89.0%

(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (726192-33-2) → (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester (726192-26-3)

Guidance literature:

With trifluoroacetic acid; In water; for 2h;

DOI:10.1021/jo049637h

Reference yield:

D-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyproline (726192-17-2) → (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester (726192-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / PyAOP; diisopropylethylamine / dimethylformamide / 1 h

2: 89 percent / trifluoroacetic acid / H₂O / 2 h

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In water; N,N-dimethyl-formamide;

DOI:10.1021/jo049637h

Reference yield: 70.0%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + (S)-2-[((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyric acid benzyl ester (726192-26-3) → (S)-2-({(2R,3S,4R,5R)-1-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionyl]-3,4-dihydroxy-5-hydroxymethyl-pyrrolidine-2-carbonyl}-amino)-3-methyl-butyric acid benzyl ester

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 1h;

DOI:10.1021/jo049637h

upstream raw materials:

(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

D-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyproline

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