169105-89-9

Basic information

• Product Name: ISOFAGOMINE, HYDROCHLORIDE
• Synonyms: ISOFAGOMINE, HYDROCHLORIDE;(3R,4R,5R)-5-(HYDROXYMETHYL)-3,4-PIPERIDINEDIOL, HYDROCHLORIDE;(3R,4R,5R)-5-(Hydroxymethyl)-3,4-piperidinediol,HCl;IsofagomineHydrochlroide;(3R,4R,5R)-5-(Hydroxymethyl)piperidine-3,4-diol hydrochloride;(3R,4R,5R)-5-(Hydroxymethyl)piperidine-3,4-diol;3,4-Piperidinediol, 5-(hydroxymethyl)-, (3R,4R,5R)-;5-Hydroxymethyl-3,4-piperidinediol
• CAS NO: 169105-89-9
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 183.63
• Product Categories: pharmacetical;Inhibitors
• Mol File: 169105-89-9.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 317.2 °C at 760 mmHg
• Flash Point: 171.8 °C
• Appearance: yellow low-melting solid
• Density: 1.279g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: 2-8°C(protect from light)
• PKA: 14.19±0.60(Predicted)
• CAS DataBase Reference: ISOFAGOMINE, HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOFAGOMINE, HYDROCHLORIDE(169105-89-9)
• EPA Substance Registry System: ISOFAGOMINE, HYDROCHLORIDE(169105-89-9)

Safety Data

• Hazardous Substances Data: 169105-89-9(Hazardous Substances Data)

Usage

Description

ISOFAGOMINE, HYDROCHLORIDE is a chemical compound that acts as a selective and potent inhibitor of β-Glycosidases, with a Ki value of 0.11 μM. It is known for its strong inhibitory effects on these enzymes, which play a crucial role in various biological processes.

Uses

Used in Pharmaceutical Industry:
ISOFAGOMINE, HYDROCHLORIDE is used as a selective inhibitor for β-Glycosidases in the pharmaceutical industry. Its application is primarily due to its ability to inhibit these enzymes, which can be beneficial in the development of drugs targeting specific diseases and conditions.
Used in Research and Development:
In the field of research and development, ISOFAGOMINE, HYDROCHLORIDE is used as a research tool to study the role of β-Glycosidases in various biological processes. Its strong inhibitory action allows scientists to investigate the effects of these enzymes on cellular functions and their potential as therapeutic targets.
Used in Enzyme Inhibition Studies:
ISOFAGOMINE, HYDROCHLORIDE is also used in enzyme inhibition studies to understand the interactions between the compound and the target enzyme. This information can be valuable in the design of new drugs and therapies that target β-Glycosidases.
Used in Biochemical Assays:
In biochemical assays, ISOFAGOMINE, HYDROCHLORIDE is employed as a specific inhibitor of β-Glycosidases, allowing researchers to measure the activity of these enzymes in various samples. This can be useful in diagnosing certain conditions or evaluating the effectiveness of other treatments.

InChI:InChI=1/C6H13NO3/c8-3-4-1-7-2-5(9)6(4)10/h4-10H,1-3H2/t4-,5+,6+/m0/s1

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

• 919364-56-0 (3R,4R,5R)-5-(hydroxymethyl)-3,4-piperidinediol L-(+)-tartrate salt 
• 215724-77-9 N-benzyl (+)-isofagomine 
• 215725-53-4 (3R,4R,5R)-1-benzyl-3-(benzyloxy)-5-(hydroxymethyl)piperdin-4-ol 
• 568586-70-9 (3R,4R,5R)-3-acetoxy-5-acetoxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine 
• 568586-68-5 (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine 
• 568586-67-4 (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-[(tetra-O-acetyl-β-D-glucopyranosyl)oxy]piperidine 
• 1333317-41-1 (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine 
• 1333317-40-0 (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine 
• 568586-63-0 (3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine 
• 215724-72-4 (3R,4R,5R)-5-hydroxymethyl-1-(4-N,N-diphenylaminobenzyl)-3,4-piperidinediol 
• 215724-61-1 (3R,4R,5R)-3-(3,4-Dihydroxy-5-hydroxymethyl-piperidin-1-yl)propionic acid 

Relevant articles and documents

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

Asymmetric synthesis of all stereoisomers of isofagomine using [2,3]-Wittig rearrangement

The asymmetric synthesis of all stereoisomers of isofagomine from 5-hydroxymethyl-3-piperidene 6, which was prepared by [2,3 ]-Wittig rearrangement of O-alkylstannylmethyl compound 5 derived from readily available chiral 3-hydroxypiperidene 4, is describe

Synthesis of (+)-isofagomine

The synthesis of (+)-isofagomine 1 using 4-pentenol 3 as a chiral precursor is described herein.

Acceleration effect of an allylic hydroxy group on ring-closing enyne metathesis of terminal alkynes: Scope, application, and mechanistic insights

An interesting acceleration effect of an allylic hydroxy group on ring-closing enyne metathesis has been found. Ring-closing enyne metathesis of terminal alkynes possessing an allylic hydroxy group proceeded smoothly without the ethylene atmosphere generally necessary to promote the reaction. The synthesis of (+)-isofagomine with the aid of this efficient reaction has been demonstrated. Mechanistic studies of the acceleration effect were also carried out. Results of NMR studies suggested that the reaction proceeded via an "ene-then-yne" pathway. Kinetic studies indicated switching of the rate-determining step as a consequence of the presence of an allylic hydroxy group. These results suggest acceleration of the reentry step of Ru-carbene species by the allylic hydroxy group.