D-Proline, 3,4-dihydroxy-, (3R,4S)-rel- (9CI)

Base Information

• Chemical Name: D-Proline, 3,4-dihydroxy-, (3R,4S)-rel- (9CI)
• CAS No.: 17663-44-4
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.131
• Mol file: 17663-44-4.mol

Synonyms:Proline,3,4-dihydroxy-, DL-cis-2,3,cis-2,4- (8CI);2,3-cis-3,4-cis-3,4-dihydroxy-DL-proline

Chemical Property of D-Proline, 3,4-dihydroxy-, (3R,4S)-rel- (9CI)

Chemical Property:

• PSA: 89.79000
• LogP: -1.90660

Purity/Quality:

99% ^*data from raw suppliers

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Technology Process of D-Proline, 3,4-dihydroxy-, (3R,4S)-rel- (9CI)

There total 13 articles about D-Proline, 3,4-dihydroxy-, (3R,4S)-rel- (9CI) 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: 94.0%

1-benzyl-(2RS)-(hydroxymethyl)pyrrolidine-(3SR,4RS)-diol → (+/-)-2,3-cis-3,4-cis-3,4-Dihydroxy-D,L-prolin (17663-43-3,17663-44-4,23161-63-9,63121-50-6,74644-88-5,95341-64-3,95341-65-4,103366-25-2,103366-26-3,105118-17-0,111766-79-1,138258-69-2,654083-19-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 4h; under 760 Torr; Ambient temperature;

Reference yield: 90.0%

(2S,3S,4R)-3,4-Diacetoxy-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester → (2RS,3SR,4RS)-3,4-dihydroxyproline (17663-43-3,17663-44-4,23161-63-9,63121-50-6,74644-88-5,95341-64-3,95341-65-4,103366-25-2,103366-26-3,105118-17-0,111766-79-1,138258-69-2,654083-19-9)

Guidance literature:

With hydrogenchloride; for 18h; Heating;

DOI:10.3987/com-97-7974

Reference yield: 83.0%

2,5-imino-2,5-dideoxy-3,4-O-isopropylidene-DL-ribo-pentononitrile → (2RS,3SR,4RS)-3,4-dihydroxyproline (17663-43-3,17663-44-4,23161-63-9,63121-50-6,74644-88-5,95341-64-3,95341-65-4,103366-25-2,103366-26-3,105118-17-0,111766-79-1,138258-69-2,654083-19-9)

Guidance literature:

With hydrogenchloride; at 50 ℃;

DOI:10.1002/hlca.19950780510

upstream raw materials:

(2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol

1-benzyl-(2SR)-(methoxycarbonyl)pyrrolidine-(3SR,4RS)-diyl carbonate

(2SR)-methoxycarbonyl-1-tosylpyrrolidine-(3SR,4RS)-diyl carbonate

(2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol

Downstream raw materials:

(2S,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine

(2R,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine

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