169105-89-9

Basic information

• Product Name: Isofagomine
• 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

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(CAS DataBase Reference)
• NIST Chemistry Reference: Isofagomine(169105-89-9)
• EPA Substance Registry System: Isofagomine(169105-89-9)

Safety Data

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

Usage

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 
• 125097-83-8 methyl 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate 
• 124988-77-8 (2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-prop-2-en-1-ol 
• 1105054-25-8 1-tert-butoxycarbonyl-5-(hydroxymethyl)piperidine-3,4-diol 
• 1353742-29-6 (3R,4R,5R)-1,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)piperidine 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 191480-69-0 (3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene 
• 1369810-85-4 tert-butyl (3R,4R)-3,4-bis(benzyloxy)-5-hydroxy-2-methylenepentylcarbamate 

Downstream Products

• 168921-63-9 (3R,4R,5R)-5-Hydroxymethyl-1-[2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-piperidine-3,4-diol 
• 19996-02-2 10-chloro-9-anthracenemethanol 
• 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 
• 215724-72-4 (3R,4R,5R)-5-hydroxymethyl-1-(4-N,N-diphenylaminobenzyl)-3,4-piperidinediol 
• 919364-56-0 (3R,4R,5R)-5-(hydroxymethyl)-3,4-piperidinediol L-(+)-tartrate salt 
• 568586-63-0 (3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine 
• 1333317-40-0 (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine 
• 1333317-41-1 (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine 
• 568586-67-4 (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-[(tetra-O-acetyl-β-D-glucopyranosyl)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 
• 568586-70-9 (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 

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

Asymmetrized tris(hydroxymethyl)methane as precursor of iminosugars: Application to the synthesis of isofagomine

A new synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM*), readily obtained in both enantiomeric forms through a chemoenzymatic procedure, is reported. In this case THYM* precursor 3 was elaborated by ring closing metathesis into some enantiopure branched tetrahydropyridines, that have been used as precursors of the potent glycosidase inhibitor isofagomine 28.

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.

Aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a versatile strategy towards synthesis of isofagomine and related biologically important azasugars

Synthesis of isofagomine has been achieved by implementation of aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a key step. The above rearrangement has also been utilized in the synthesis of biologically important polyhydroxylated piperidine frameworks such as isogalactofagomine, ent-isogalactofagomine and their analogues and some other azasugars as glycosidase inhibitors. The Royal Society of Chemistry 2012.

Asymmetric synthesis of polyhydroxylated N -alkoxypiperidines by ring-closing double reductive amination: Facile preparation of isofagomine and analogues

A de novo synthesis of novel polyhydroxylated N-alkoxypiperidines based on the ring-closing double reductive amination of 1,5-dialdehydes, obtained by oxidative cleavage of cyclopentene derivatives, with O-substituted hydroxylamines is reported. Isofagomine was accessed by cleavage of the N-O bond of an N-alkoxypiperidine.

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.

NEW METHOD FOR PREPARING ISOFAGOMINE AND ITS DERIVATIVES

A method for preparing isofagomine, its derivatives, intermediates and salts thereof using novel processes to make isofagomine from D-(-)-arabinose and L-(-)-xylose.

Tartrate sale of isofagomine and methods of use

A novel tartaric acid salt of Isafagomine (Isofagomine tartrate) that can be used for the treatment of Gaucher disease is provided. The invention also provides a crystalline form of isofagomine tartrate, method for preparing the salt, a pharmaceutical composition containing the salt, and a method of treating Gaucher disease.

Asymmetrized tris(hydroxymethyl)methane as a precursor of N- And O-containing 6-membered heterocycles through ring-closing metathesis

A novel synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM*) 1, obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor 3, N- and O-containing 6-membered heteroc