654083-19-9

Basic information

• Product Name: Proline, 3,4-dihydroxy-, (3S,4R)- (9CI)
• Synonyms: Proline, 3,4-dihydroxy-, (3S,4R)- (9CI)
• CAS NO: 654083-19-9
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.12926
• Product Categories: CARBOXYLICACID;ALCOHOL
• Mol File: 654083-19-9.mol
• Article Data: 37

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Proline, 3,4-dihydroxy-, (3S,4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Proline, 3,4-dihydroxy-, (3S,4R)- (9CI)(654083-19-9)
• EPA Substance Registry System: Proline, 3,4-dihydroxy-, (3S,4R)- (9CI)(654083-19-9)

Safety Data

• Hazardous Substances Data: 654083-19-9(Hazardous Substances Data)

Upstream product

• 17645-37-3 N-Tosyl-2,3-trans-3,4-trans-3,4-dihydroxy-L-prolin 
• 138228-39-4 (3S,4S)-3,4-dibenzoyloxy-2-cyanopyrrolidine 
• 138228-52-1 (2R,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 
• 1577180-41-6 (3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-methoxycarbonyl-2-pyrrolidinone 
• 1577180-42-7 (2R,3S,4S)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-2-methoxycarbonylpyrrolidine 
• 1577468-54-2 1-benzyl-3,4-dihydroxyproline hydrochloride 
• 1577180-45-0 (3R,4S,5S)-1-benzyl-5-cyano-3,4-diacetoxy-2-pyrrolidinone 
• 4298-08-2 trans-3-hydroxy-L-proline 
• 105016-02-2 ((3S,4R,5S)-5-Bromomethyl-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester 
• 101623-96-5 (2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-pent-4-enoic acid 
• 294211-59-9 Toluene-4-sulfonic acid (2R,3R,4S)-4-benzyloxycarbonylamino-3-hydroxy-5-oxo-tetrahydro-furan-2-ylmethyl ester 
• 294211-56-6 (2S,3R)-2-Benzyloxycarbonylamino-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionic acid methyl ester 
• 294211-58-8 ((3S,4R,5R)-4-Hydroxy-5-hydroxymethyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester 
• 294211-55-5 (S)-2-Amino-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionic acid 

Downstream Products

• 138228-51-0 (2S,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 
• 138228-52-1 (2R,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 

Relevant articles and documents

Synthesis of l-2,3-trans-3,4-cis-dihydroxyproline building blocks for peptide synthesis

L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O- isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.

Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles

Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable, as yet largely untapped, potential for amino acid hydroxylases and other 2OG oxygenases in biocatalysis.

Diversity oriented concise asymmetric synthesis of azasugars: A facile access to l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine

Diversity oriented concise asymmetric syntheses of l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine have been developed from (R)-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de. The (2R,3R,4S)-2,3-dihydroxypentanoate derivative 15 was subsequently converted to natural pyrrolidine azasugar 1 and non-natural piperidine azasugar 4 under cascade reaction conditions in good yields.