Migalastat

Base Information

• Chemical Name: Migalastat
• CAS No.: 108147-54-2
• Molecular Formula: C6H13 N O4
• Molecular Weight: 199.63
• UNII: C4XNY919FW
• DSSTox Substance ID: DTXSID201022520
• Nikkaji Number: J370.938H
• Wikipedia: Migalastat
• Wikidata: Q161613
• NCI Thesaurus Code: C78120
• RXCUI: 2054252
• Pharos Ligand ID: Y1A2RHTFZYAL
• Metabolomics Workbench ID: 149374
• ChEMBL ID: CHEMBL110458
• Mol file: 108147-54-2.mol

Synonyms:1-butyl-2-(hydroxylmethyl)piperidine-3,4,5-triol;1-deoxy-galactonojirimycin;1-deoxygalacto-nojirimycin;1-deoxygalactonojirimycin;AT1001 deoxyjirimycin;Galafold;GR181413A;lucerastat;migalastat;migalastat HCl;migalastat hydrochloride;N-butyldeoxygalacto-nojirimycin;N-butyldeoxygalactonojirimycin;NB-DGJ

Chemical Property of Migalastat

Chemical Property:

• Vapor Pressure: 1.13E-06mmHg at 25°C
• Melting Point: 243-245 °C
• Boiling Point: 361.1°C at 760 mmHg
• PKA: 13.77±0.70(Predicted)
• Flash Point: 197.3°C
• PSA: 92.95000
• Density: 1.456g/cm³
• LogP: -2.63800
• Storage Temp.: 2-8°C
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 163.08445790
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Genetic Disorder Agents
• Canonical SMILES: C1C(C(C(C(N1)CO)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H]([C@H]([C@H](N1)CO)O)O)O
• Recent ClinicalTrials: A Study to Evaluate the Effect of Venglustat Tablets on Left Ventricular Mass Index in Male and Female Adult Participants With Fabry Disease
• Recent EU Clinical Trials: A randomized, open-label, parallel-group, 18-month Phase 3 study to evaluate the effect of venglustat compared with usual standard of care on left ventricular mass index in participants with Fabry disease and left ventricular hypertrophy

Technology Process of Migalastat

There total 163 articles about Migalastat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-Benzhydryl-1-deoxymannojirimycin (149339-06-0) → 1-deoxymannojirimycin (14199-63-4,16647-80-6,19130-96-2,84444-90-6,84518-54-7,108147-54-2,117821-07-5,126663-71-6,135246-66-1,135395-59-4,143406-74-0,146747-37-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 30h; under 2585.7 Torr;

DOI:10.1021/jo00090a040

Reference yield: 100.0%

3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol (94119-08-1) → 1-deoxymannojirimycin (14199-63-4,16647-80-6,19130-96-2,84444-90-6,84518-54-7,108147-54-2,117821-07-5,126663-71-6,135246-66-1,135395-59-4,143406-74-0,146747-37-7)

Guidance literature:

With hydrogen; acetic acid; palladium; for 18h;

DOI:10.1016/S0968-0896(96)00266-0

Reference yield: 94.5%

2,4-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol (121195-27-5) → 1-deoxymannojirimycin (14199-63-4,16647-80-6,19130-96-2,84444-90-6,84518-54-7,108147-54-2,117821-07-5,126663-71-6,135246-66-1,135395-59-4,143406-74-0,146747-37-7)

Guidance literature:

With hydrogen; palladium; In acetic acid; for 18h; under 760 Torr;

DOI:10.1016/0040-4020(89)80060-2

upstream raw materials:

dihydroxyacetone phosphate

(RS)-3-azido-2-hydroxypropanal

dihydroxyacetone

5-Azido-3,6-di-O-benzyl-5-deoxy-α/β-D-glucofuranose

Downstream raw materials:

1,5-dideoxy-1,5-(methyliminiumyl)-D-mannitol

N-butyl-1-deoxygalactonojirimycin

N-nonyl 1-deoxygalactonojirimycin

(2R,3S,4R,5S)-1-(5-(((3R,5R,7R)-adamantan-1-yl)methoxy)pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

Refernces

Synthesis of (+)-1,5-dideoxy-1,5-imino-D-galactitol, a potent α-D-galactosidase inhibitor

10.1016/0008-6215(87)80289-6

The research aimed to develop an efficient, enantio-specific, total synthesis of 1,5-dideoxy-1,5-imino-D-galactitol (1), a potent and selective α-D-galactosidase inhibitor. The purpose of this synthesis was to probe questions of enzyme stereo-selectivity and mechanism, and to potentially aid in developing biochemical and clinical models for pathological conditions related to α-D-galactosidase deficiencies, such as Fabry's disease. The synthesized compound 1 was found to competitively inhibit the hydrolysis of p-nitrophenyl α-D-galactopyranoside by green coffee-bean α-galactosidase and showed significant inhibitory effects against human-placental ceramide trihexosidase, the α-D-galactosidase implicated in Fabry’s disease.