275363-98-9

Basic information

• Product Name: 3,4-Piperidinediol, 5-(hydroxymethyl)-, (3R,4S,5S)-rel- (9CI)
• Synonyms: 3,4-Piperidinediol, 5-(hydroxymethyl)-, (3R,4S,5S)-rel- (9CI)
• CAS NO: 275363-98-9
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.17232
• Product Categories: ALCOHOL
• Mol File: 275363-98-9.mol
• Article Data: 40

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-Piperidinediol, 5-(hydroxymethyl)-, (3R,4S,5S)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Piperidinediol, 5-(hydroxymethyl)-, (3R,4S,5S)-rel- (9CI)(275363-98-9)
• EPA Substance Registry System: 3,4-Piperidinediol, 5-(hydroxymethyl)-, (3R,4S,5S)-rel- (9CI)(275363-98-9)

Safety Data

• Hazardous Substances Data: 275363-98-9(Hazardous Substances Data)

Upstream product

• 1026346-29-1 (3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine-3,4-diol 
• 215724-77-9 N-benzyl (+)-isofagomine 
• 323201-27-0 (3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-piperidine-1-carboxylic acid phenyl ester 
• 215725-62-5 tert-butyl 3-hydroxymethyl-4,5-epoxypiperidine-1-carboxylate 
• 855298-05-4 (5R)-5-hydroxymethyl-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester 
• 1026939-30-9 (2R,3S,4R,5R)-5-Aminomethyl-2-benzyloxy-tetrahydro-pyran-3,4-diol 
• 858614-82-1 (3R,4R,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine 
• 852213-67-3 benzyl 4-cyano-4-deoxy-2,3-O-isopropylidene-β-D-arabinopyranoside 
• 521917-99-7 (R,E)-2-azidomethyl-5-methylhex-3-en-1-ol 
• 521917-97-5 (R,E)-2-azidomethyl-5-methylhex-3-enyl ester acetate 
• 855298-13-4 (S,E)-2-(methanesulfonyloxy)methyl-5-methylhex-3-enyl acetate 
• 521918-00-3 (R,E)-(2-hydroxymethyl-5-methylhex-3-enyl) carbamic acid tert-butyl ester 
• 521918-08-1 (R)-3-[(triisopropylsilyloxy)methyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 521918-03-6 (R,E)-5-methyl-2-[(triisopropylsilyloxy)methyl]hex-3-enyl carbamic acid tert-butyl ester 

Downstream Products

• 957230-65-8 (3R,4R,5R)-5-(hydroxymethyl)-3,4-piperidinediol L-(+)-tartrate salt 
• 957230-65-8 (3R,4R,5R)-5-(hydroxymethyl)-3,4-piperidinediol D-(-)-tartrate salt 
• 957230-65-8 isofagomine D-tartrate 
• 215724-61-1 (3R,4R,5R)-3-(3,4-Dihydroxy-5-hydroxymethyl-piperidin-1-yl)propionic acid 
• 919364-56-0 (3R,4R,5R)-5-(hydroxymethyl)-3,4-piperidinediol L-(+)-tartrate salt 
• 215725-53-4 (3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol 

Relevant articles and documents

Synthesis of Isofagomine Derivatives as New Fluorescence pH Indicators/Glycosidase Inhibitors

Inhibitor protonation of azasugars of the isofagomine type when bound to enzyme can be investigated using photon induced electron transfer (PET) quenching of an attached fluorophore. For this purpose, Isofagomine, iso-d-galacto-fagomine, and iso-l-gulo-fagomine were converted to N-(10-chloroanthracenenyl-9-alkyl) derivatives where the alkyl group contained one, two, or three methylene groups. The new derivatives displayed pH dependent fluorescence; as the ammonium forms they were fluorescent, while 90–99 percent of the fluorescence was quenched in the amine forms. The 3 isofagomine derivatives were competitive inhibitors of T. Maritima Ι-glucosidase with Ki values from 0.37–4.6ΤM. Similarly, the iso-d-galacto-fagomines inhibited A. Niger Ι-galactosidase with Ki values from 63–2000 nm. When bound to the enzymes the inhibitors displayed between 1–15 percent fluorescence.

A divergent approach for the synthesis of some polyhydroxy pyrrolidines and piperidines from ribosylamine

A simple and efficient synthesis of 1,4-dideoxy-1,4-imino-d-ribitol, 1,4-dideoxy-1,4-imino-l-lyxitol, N-benzyl derivative of d-ribitol, 3,4,5-trihydroxy-piperidine, l-4-epi-isofagomine and d-3-epi-isofagomine, which are glycosidase inhibitors has been described from the commercially available d-ribose as a starting material.

Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins

The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from d-mannitol, has been carried out. Two different synthetic strategies were followed for e