1-Deoxymannojirimycin hydrochloride

Base Information

• Chemical Name: 1-Deoxymannojirimycin hydrochloride
• CAS No.: 73465-43-7
• Molecular Formula: C₆H₁₃NO₄*ClH
• Molecular Weight: 199.634
• Hs Code.: 2941900000
• European Community (EC) Number: 635-313-7
• ChEMBL ID: CHEMBL4303328
• DSSTox Substance ID: DTXSID00994213
• Mol file: 73465-43-7.mol

Synonyms:1-Deoxymannojirimycin hydrochloride;73465-43-7;deoxymannojirimycin hydrochloride;1-Deoxymannojirimycin (hydrochloride);(2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride;84444-90-6;3,4,5-Piperidinetriol, 2-(hydroxymethyl)-, hydrochloride, (2R,3R,4R,5R)-;(2R,3R,4R,5R)-2-(Hydroxymethyl)-3,4,5-piperidinetriol Hydrochloride;(+)-1-Deoxynojirimycin hydrochloride;1-Deoxymannojirimycin HCl;1,5-Dideoxy-1,5-imino-D-mannitol hydrochloride;Deoxymannojirimycin HCl;Deoxymannonojirimycin HCl;C6H13NO4.HCl;SCHEMBL951723;CHEMBL4303328;DTXSID00994213;HMS3412C16;HMS3676C16;HB4598;MFCD00083611;AKOS024456495;CS-W010499;HY-W009783;(+)-1-Deoxymannojirimycin hydrochloride;1-Deoxymannojirimycin hydrochloride (DMM);AS-76184;F85604;A909720;SR-01000597908;SR-01000597908-1;W-203675;2-(Hydroxymethyl)piperidine-3,4,5-triol--hydrogen chloride (1/1);(2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol;hydrochloride;(2R,3R,4R,5R)-2-(hydroxymethyl)piperidine-3,4,5-triolhydrochloride

Chemical Property of 1-Deoxymannojirimycin hydrochloride

Chemical Property:

• Melting Point: 183-185°C
• PSA: 92.95000
• LogP: -1.83600
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble10mg/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

Deoxymannojirimycin, Hydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-37/39-26

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
• Description: 1-Deoxymannojirimycin is a specific inhibitor of class I α-1,2-mannosidase (IC50 = 0.02 μM), a key enzyme for N-glycan processing in the endoplasmic reticulum and Golgi and for targeting misfolded proteins for translocation out of the endoplasmic reticulum and degradation by the proteasome. By inhibiting α-1,2-mannosidase activity, this compound generates N-linked oligosaccharides with high mannose content, preventing misfolded protein degradation. This compound has been used for studies on glycoprotein processing and as a model for the development of anticancer and antiviral therapies.
• Uses: Deoxymannojirimycin has been shown to be a potent inhibitor of the mammalian Golgi alpha- mannosidase 1 activity, blocking the conversion of high-mannose oligosaccharides to complex-type oligosaccharides. However, it does not inhibit the biosynthesis of lipid- linked oligosaccharides. Selective inhibitor of a-mannosidase

Technology Process of 1-Deoxymannojirimycin hydrochloride

There total 1 articles about 1-Deoxymannojirimycin 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