(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester

Base Information

• Chemical Name: (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester
• CAS No.: 111193-60-3
• Molecular Formula: C₁₄H₁₇NO₆
• Molecular Weight: 295.292
• Mol file: 111193-60-3.mol

Synonyms:

Chemical Property of (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester

There total 9 articles about (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline 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: 78.0%

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5) → (S)-3,4-Dihydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (111193-60-3,111193-61-4,138228-51-0,138228-52-1,147316-05-0)

Guidance literature:

osmium(VIII) oxide; In water; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)95775-7

Reference yield:

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5) → (2S,3S,4R)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester + (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester (111193-60-3)

Guidance literature:

With osmium(VIII) oxide; dihydrogen peroxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; at 50 ℃; Title compound not separated from byproducts;

DOI:10.1016/0008-6215(94)84059-8

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) → (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester (111193-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Et₃N / dimethylformamide

2: OsO₄, 30percent H₂O₂, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 50 °C

With osmium(VIII) oxide; dihydrogen peroxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/0008-6215(94)84059-8

upstream raw materials:

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester

(R)-4-hydroxy-L-proline ethyl ester

N-(Benzyloxycarbonyloxy)succinimide

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

(3aR,4R,6aS)-2,2-Dimethyl-4-(toluene-4-sulfonyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

(3aR,4S,6aS)-4-((S)-3-Amino-3-carboxy-propylsulfanylmethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

(3aR,4S,6aS)-2,2-Dimethyl-4-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

(2R,3R,4S)-1-benzyloxycarbonyl-2-hydroxymethylpyrrolidine-3,4-diol

Refernces

• 1、 Guillerm,Varkados,Auvin,Le Goffic. "Synthesis of hydroxylated pyrrolidines derivatives as potential inhibitors of SAH/MTA nucleosidase". . p. 535 - 538. Retrieved 2007/10/02.