(S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 203186-05-4
• Molecular Formula: C₁₅H₁₉NO₇
• Molecular Weight: 325.318
• Mol file: 203186-05-4.mol

Synonyms:

Chemical Property of (S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

There total 1 articles about (S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid 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: 92.0%

(S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester (187087-43-0) → (S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester (203186-05-4)

Guidance literature:

(S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/jo990140v

Reference yield: 50.0%

allyl bromide (106-95-6) + (S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester (203186-05-4) → (S)-1-[(1S,3aS,4R,5R,6aS)-1-Allyl-5-((S)-1-hydroxy-but-3-enyl)-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester + (S)-1-[(1R,3aS,4R,5R,6aS)-1-Allyl-5-((S)-1-hydroxy-but-3-enyl)-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester (241824-35-1)

Guidance literature:

With indium; In hydrogenchloride; ethanol; for 14h;

DOI:10.1021/jo990140v

Reference yield:

(S)-1-((3aS,4R,5R,6aS)-5-Formyl-1-hydroxy-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester (203186-05-4) → (S)-1-[(3aS,4R,5R,6aS)-5-(4-Bromo-benzoyloxymethyl)-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / sodium borohydride / methanol / 5 h / 20 °C

2: 100 percent / CHCl₃ / 48 h / 20 °C

3: 84 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

With sodium tetrahydroborate; triethylamine; In methanol; dichloromethane; chloroform; 1: Reduction / 2: Isomerization / 3: Esterification;

DOI:10.1021/jo990140v

upstream raw materials:

(S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(S)-1-[(1R,3aS,4R,5R,6aS)-1-Allyl-5-((S)-1-hydroxy-but-3-enyl)-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester

(S)-1-((3aS,4R,5R,6aS)-5-Hydroxymethyl-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

(S)-1-((3aS,4R,5R,6aS)-5-Formyl-3-oxo-hexahydro-cyclopenta[c]furan-4-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester