113571-59-8

Basic information

• Product Name: (2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
• Synonyms: (2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
• CAS NO: 113571-59-8
• Molecular Weight: 263.337
• Mol File: 113571-59-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol(113571-59-8)
• EPA Substance Registry System: (2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol(113571-59-8)

Safety Data

• Hazardous Substances Data: 113571-59-8(Hazardous Substances Data)

Upstream product

• 132430-66-1 (3S,4S,5R)-1-benzyl-5-hydroxymethyl-3,4-isopropylidenedioxy-2-pyrrolidinone 
• 17342-08-4 (S)-Pyroglutaminol 
• 132430-67-2 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol 
• 84709-46-6 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol 
• 125629-92-7 (S)-1-benzyl-5-((benzyloxy)methyl)pyrrolidin-2-one 
• 100-39-0 benzyl bromide 
• 100-46-9 benzylamine 
• 163592-81-2 (2R,3S)-N-benzyl-N-benzoyl-2,3-O-isopropylidene-4-ene-pentylamine 
• 138609-71-9 (2R,3S)-N-benzyl-N-benzoyl-2,3-dihydroxy-4-ene-pentylamine 
• 123533-17-5 (2R,3S)-1-(benzylamino)pent-4-ene-2,3-diol 
• 922-65-6 divinylcarbinol 
• 132430-78-5 (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine 
• 132430-68-3 (2R,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-(trityloxymethyl)-pyrrolidine 
• 113571-62-3 (3S,4S,5R)-1-benzyl-5-benzyloxymethyl-3,4-dihydroxy-2-pyrrolidinone 

Downstream Products

• 72741-87-8 swainsonine 
• 113626-57-6 (2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-hydroxymethylpyrrolidine 
• 132430-76-3 (3aS,4R,6aR)-5-Benzyl-4-((R)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 113626-58-7 (2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine 
• 113626-61-2 (2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>pyrrolidine 
• 132430-77-4 (R)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol 
• 132561-50-3 (2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-2-((S)-1-benzyloxy-but-3-enyl)-pyrrolidine 
• 113626-59-8 (2R,3S,4R)-N-benzyl-2-<(1R)-1-benzyloxy-3-butenyl>-3,4-bis(benzyloxy)pyrrolidine 
• 132561-49-0 (S)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-benzyloxy-butan-1-ol 
• 113626-62-3 (2R,3S,4R)-N-benzyl-2-<(1R)-1-benzyloxy-4-hydroxybutanyl>-3,4-bis(benzyloxy)pyrrolidine 
• 113200-95-6 (1S,2R,8S,8aR)-4-Benzyl-1,2,8-tris-benzyloxy-octahydro-indolizinium; chloride 
• 113626-63-4 (1S,2R,8R,8aR)-4-Benzyl-1,2,8-tris-benzyloxy-octahydro-indolizinium; chloride 
• 117719-26-3 (2R,3S,4R)-3,4-dihydroxy-2-(methoxymethoxy)methyl-N-benzylpyrrolidine 
• 117736-94-4 (2R,3S,4R)-3,4-dibenzyloxy-2-(methoxymethoxy)methyl-N-benzylpyrrolidine 

Relevant articles and documents

Tuning of β-glucosidase and α-galactosidase inhibition by generation and in situ screening of a library of pyrrolidine-triazole hybrid molecules

The preliminary screening of two libraries of epimeric (pyrrolidin-2-yl)triazoles (14a-s and 22a-s), generated via click chemistry, allowed the rapid identification of four α-galactosidase (coffee beans) inhibitors (22b,k,p,r) and two β-glucosidase (almond) inhibitors (14b,f) in the low μM range. The additional biological analysis of 14b,f towards β-glucocerebrosidase (human lysosomal β-glucosidase), as target enzyme for Gaucher disease, showed a good correlation with the inhibition results obtained for the plant (almond) enzyme. Surprisingly, although these compounds showed inhibition towards β-glucocerebrosidase as acid hydrolase, they did not inhibit bovine liver β-glucosidase as neutral hydrolase. In contrast to what was observed for β-glucosidase inhibition, the coffee bean α-galactosidase inhibitors of the epimeric library (22b,k,p,r) only showed weak inhibition towards human lysosomal α-galactosidase.

A SYNTHESIS OF THE POLYHYDROXYLATED PYRROLIDINES: SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND N-BENZYL-4-EPI-(-)-ANISOMYCIN

A synthesis of 1,4-dideoxy-1,4-imino-D-lyxitol and N-benzyl-4-epi-(-)anisomycin was described.

Synthesis of (-)-swainsonine and optically active 3,4-dihydroxy-2-hydroxymethylpyrrolidines.

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