Duvoglustat hydrochloride

Base Information

• Chemical Name: Duvoglustat hydrochloride
• CAS No.: 73285-50-4
• Molecular Formula: C₆H₁₃NO₄*ClH
• Molecular Weight: 199.634
• European Community (EC) Number: 615-948-6
• UNII: 0RN23C42QR
• ChEMBL ID: CHEMBL460785
• DSSTox Substance ID: DTXSID401017351
• NCI Thesaurus Code: C87374
• Mol file: 73285-50-4.mol

Synonyms:1 Deoxymannojirimycin;1 Deoxynojirimycin;1 Deoxynojirimycin Hydrochloride;1,5-Deoxy-1,5-imino-D-mannitol;1,5-Dideoxy-1,5-imino-D-mannitol;1-Deoxymannojirimycin;1-Deoxynojirimycin;1-Deoxynojirimycin Hydrochloride;Bay n 5595;Moranoline

Chemical Property of Duvoglustat hydrochloride

Chemical Property:

• Vapor Pressure: 1.98E-07mmHg at 25°C
• Melting Point: 195-196 °C
• Boiling Point: 382.7 °C at 760 mmHg
• Flash Point: 185.2 °C
• PSA: 92.95000
• Density: 1.456 g/cm3
• LogP: -1.83600
• Storage Temp.: 2-8°C
• Solubility.: Water (Slightly)
• Water Solubility.: Soluble in water at 20mg/ml
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 199.0611356
• Heavy Atom Count: 12
• Complexity: 132

Purity/Quality:

98%, ^*data from raw suppliers

DNM1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(N1)CO)O)O)O.Cl
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H](N1)CO)O)O)O.Cl
• Recent EU Clinical Trials: AN OPEN-LABEL MULTI-CENTER, INTERNATIONAL STUDY TO INVESTIGATE DRUG-DRUG INTERACTIONS BETWEEN AT2220 AND ALGLUCOSIDASE ALFA IN PATIENTS WITH POMPE DISEASE
• Description: 1-Deoxynojirimycin (1-DNJ) is an iminosugar that has been found in M. alba (mulberry) leaves and has diverse biological activities. It inhibits the activities of α- and β-glucosidase (IC50s = 35 and 71 μM, respectively). 1-DNJ (5 mM) reduces the formation of N-linked complex oligosaccharides in IEC-6 cells. It inhibits HIV-1 envelope-mediated membrane fusion in CEM cells when used at a concentration of 2 mM. 1-DNJ (1-100 μg/ml) reduces the invasion and migration of B16/F10 mouse melanoma cells. It improves glucose and insulin tolerance in db/db mice when administered intravenously at doses ranging from 20 to 80 mg/kg per day for four weeks.
• Uses: natural chitin synthase inhibitor

Technology Process of Duvoglustat hydrochloride

There total 1 articles about Duvoglustat hydrochloride 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: 16.0%

5-azido-5-deoxy-D-glucofuranose (146897-25-8) → 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2) + 1-deoxynojirimycin hydrochloride (73285-50-4,73465-43-7,75172-81-5,118464-54-3,126663-84-1,126923-63-5,136658-34-9)

Guidance literature:

5-azido-5-deoxy-D-glucofuranose; With palladium 10% on activated carbon; hydrogen; In water; at 20 ℃; under 2068.65 - 2585.81 Torr;

With hydrogenchloride; In water; pH=2;

DOI:10.1016/j.tetasy.2010.01.017

Reference yield: 86.0%

benzyloxyacetoaldehyde (60656-87-3) + 1-deoxynojirimycin hydrochloride (73285-50-4,73465-43-7,75172-81-5,118464-54-3,126663-84-1,126923-63-5,136658-34-9) → N-(2-benzyloxyethyl)-1-deoxynojirimycin (1203659-54-4)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 48h;

DOI:10.1021/jm901281m

Reference yield: 80.8%

1-deoxynojirimycin hydrochloride (73285-50-4,73465-43-7,75172-81-5,118464-54-3,126663-84-1,126923-63-5,136658-34-9) + benzyl chloroformate (501-53-1,94274-21-2) → N-Benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (130539-12-7)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 0 - 20 ℃; for 6.25h;

upstream raw materials:

5-azido-5-deoxy-D-glucofuranose

Downstream raw materials:

N-(2-benzyloxyethyl)-1-deoxynojirimycin

1,5-dideoxy-1,5-imino-D-glucitol

Refernces