(-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Base Information

• Chemical Name: (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester
• CAS No.: 648930-90-9
• Molecular Formula: C₁₉H₂₆N₂O₅
• Molecular Weight: 362.426
• Mol file: 648930-90-9.mol

Synonyms:(-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Chemical Property of (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

There total 28 articles about (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl 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: 61.0%

(2R)-2-(2-benzyloxycarbonylaminoethyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester + benzyl chloroformate (501-53-1,94274-21-2) → (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (648930-90-9) + (1S,2R,5R)-2-(2-Benzyloxycarbonylamino-ethyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Guidance literature:

(2R)-2-(2-benzyloxycarbonylaminoethyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester; With hydrogen; palladium on activated charcoal; In ethanol; at 0 - 20 ℃;

benzyl chloroformate; With sodium carbonate; In 1,4-dioxane; water; for 1h;

DOI:10.1016/j.bmc.2004.10.060

Reference yield: 60.5%

(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester (648930-89-6) + benzyl chloroformate (501-53-1,94274-21-2) → (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (648930-90-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 ℃; for 1h;

Reference yield:

3-(4-nitro-benzoyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (1257235-22-5) → (-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (648930-90-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃;

upstream raw materials:

benzyl chloroformate

(-)-(R)-2-(2-hydroxyethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

(S)-2-(2-diazoacetyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

(R)-2-(2-aminoethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester

6-hydroxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester hydrochloride salt

(1-{1-[4-benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

{1-[1-(6-benzylcarbamoyloxy-4-isopropylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-2,2-dimethyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid benzyl ester