105878-97-5

Basic information

• Product Name: (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol
• Synonyms: (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS NO: 105878-97-5
• Molecular Weight: 267.282
• Mol File: 105878-97-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol(105878-97-5)
• EPA Substance Registry System: (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol(105878-97-5)

Safety Data

• Hazardous Substances Data: 105878-97-5(Hazardous Substances Data)

Upstream product

• 96-26-4 dihydroxyacetone 
• 67561-03-9 N-benzyloxycarbonylglycinal 
• 129961-19-9 (1R,3S,4S,7R)-3-Methoxy-2-oxa-5-aza-bicyclo[2.2.1]heptan-7-ol 
• 105879-00-3 3-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucose 
• 7045-40-1 Methyl 3,5-O-Isopropylidene-α-D-xylofuranoside 
• 110088-79-4 methyl 2-azido-2-deoxy-5-O-p-toluenesulphonyl-α-D-lyxofuranoside 
• 110088-78-3 methyl 3,5-O-isopropylidene-2-O-trifluoromethanesulphonyl-α-D-xylofuranoside 
• 100806-50-6 methyl 2-azido-2-deoxy-3,5-O-isopropylidene-α-D-lyxofuranoside 
• 100896-15-9 methyl 2-azido-2-deoxy-α-D-lyxofuranoside 
• 100937-52-8 1,4-dideoxy-1,4-imino-D-arabitol 
• 501-53-1 benzyl chloroformate 
• 129492-51-9 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((phenylamino)methyl)pyrrolidine 
• 100806-51-7 methyl N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-α-D-lyxofuranoside 
• 108692-47-3 (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 

Downstream Products

• 100991-92-2 (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine hydrochloride 
• 1427173-59-8 (2R,3R,4R)-3,4-dihydroxy-2-((phenylamino)methyl)pyrrolidine 
• 1427173-61-2 (2R,3R,4R)-2-((benzylamino)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-83-8 (2R,3R,4R)-N-benzyloxycarbonyl-2-((glycineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-85-0 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-alanineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-94-1 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-valineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427174-30-8 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-leucineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-87-2 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-phenylalanineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-88-3 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)methyl)pyrrolidine 
• 1427173-96-3 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-aspartic(β^tBu)amidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-90-7 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-arginineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-92-9 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-prolineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427174-31-9 (3S,7R,8R,8aR)-3-benzyl-7,8-dihydroxyhexahydropyrrolo[1,2-a]-pyrazin-4(1H)-one 
• 129492-51-9 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((phenylamino)methyl)pyrrolidine 

Relevant articles and documents

Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives

A chemo-enzymatic strategy for the preparation of 2-aminomethyl derivatives of (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol (also called 1,4-dideoxy-1,4-imino-d-arabinitol, DAB) and its enantiomer LAB is presented. The synthesis is based on the enzymatic preparation of DAB and LAB followed by the chemical modification of their hydroxymethyl functionality to afford diverse 2-aminomethyl derivatives. This strategy leads to novel aromatic, aminoalcohol and 2-oxopiperazine DAB and LAB derivatives. The compounds were preliminarily explored as inhibitors of a panel of commercial glycosidases, rat intestinal disaccharidases and against Mycobacterium tuberculosis, the causative agent of tuberculosis. It was found that the inhibitory profile of the new products differed considerably from the parent DAB and LAB. Furthermore, some of them were active inhibiting the growth of M. tuberculosis.

Structure and synthesis of nectrisine, a new immunomodulator isolated from a fungus

The structure of a novel immunomodulator, nectrisine (1), has been elucidated on the basis of chemical and spectroscopic evidence. Its absolute stereochemistry was predicted on the basis of the dibenzoate chirality rule and finally confirmed by a synthesi

THE SYNTHESIS FROM D-XYLOSE OF THE POTENT AND SPECIFIC ENANTIOMERIC GLUCOSIDASE INHIBITORS, 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL AND 1,4-DIDEOXY-1,4-AMINO-L-ARABINITOL

Both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol are specific inhibitors of glucosidases.The synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol involves connecting C2 and C5 of xylose together with nitrogen, whereas the synthesis of 1,4-dideoxy-1,4-imino-