2-(Hydroxymethyl)piperidine-3,4,5-triol

Base Information

• Chemical Name: 2-(Hydroxymethyl)piperidine-3,4,5-triol
• CAS No.: 19130-96-2
• Molecular Formula: C6H13NO4
• Molecular Weight: 163.174
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID50864871
• Nikkaji Number: J1.676.303I
• Wikidata: Q105158746
• ChEMBL ID: CHEMBL11510
• Mol file: 19130-96-2.mol

Synonyms:1-deoxy-nojirimycin

Chemical Property of 2-(Hydroxymethyl)piperidine-3,4,5-triol

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 195-196 °C
• Refractive Index: 1.582
• Boiling Point: 361.1 °C at 760 mmHg
• PKA: 13.77±0.70(Predicted)
• Flash Point: 197.3 °C
• PSA: 92.95000
• Density: 1.456 g/cm³
• LogP: -2.63800
• Storage Temp.: Desiccate at +4°C
• Solubility.: Soluble in Water up to 25 mg/ml).
• Water Solubility.: Soluble in water, dimethyl sulfoxide and methanol.
• 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:

1-Deoxynojirimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(N1)CO)O)O)O
• Description: Deoxynojirimycin (19130-96-2) inhibits α-glucosidase I and II.1,2 Inhibits human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step.3 May be used to produce an affinity ligand for purifying glucosidase 1.4 Deoxynojirimycin was used to inhibit ER glucosidases I and II allowing for the discovery of a second mechanism for deglucosylation of N-linked oligosaccharides in PhaR1.7, a mouse lymphoma cell line.5
• Uses: Deoxynojirimycin inhibits mammalian glucosidase 1. As well, it inhibits intestinal and lysosmal alpha-glucosidases, beta-glucosidase from sweet almonds, pancreatic alpha-amylase and amyloglucosidase. An inhibitor of α-glucosidase I and II An alpha-glucosidase inhibitor. Interferes with normal processing of N-linked glycoproteins.(+)-1-Deoxynojirimycin acts as an inhibitor of alfa-glucosidase I and II and maltase-glucoamylase. It also inhibits mammalian glucosidase, intestinal and lysosmal, beta-glucosidase from sweet almonds, pancreatic alfa-amylase and amyloglucosidase. Further, it serves as a enzyme enhancer for the treatment of Fabry and Pompe disease.

Technology Process of 2-(Hydroxymethyl)piperidine-3,4,5-triol

There total 338 articles about 2-(Hydroxymethyl)piperidine-3,4,5-triol 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%

2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (69567-11-9,76738-52-8,126836-30-4) → 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2)

Guidance literature:

With hydrogenchloride; 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; water; for 14h;

DOI:10.1016/j.ejmech.2016.07.021

Reference yield: 100.0%

N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (157363-86-5) → 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2)

Guidance literature:

With hydrogen; palladium; In acetic acid; for 15h;

DOI:10.1016/S0040-4039(00)76888-2

Reference yield: 99.0%

N-Benzhydryl-1-deoxynojirimycin (132198-14-2) → 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 24h; under 3102.9 Torr;

DOI:10.1021/jo00090a040

upstream raw materials:

nojirimycin

dihydroxyacetone phosphate

(RS)-3-azido-2-hydroxypropanal

dihydroxyacetone

Downstream raw materials:

Benzoic acid (2R,3R,4R,5S)-3,4,5-trihydroxy-piperidin-2-ylmethyl ester

C₂₀H₂₁NO₆

N-benzyl-1-deoxynojirimycin

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

Refernces

Total synthesis of 3,3-difluorinated 1-deoxynojirimycin analogues

10.1016/j.tet.2009.11.069

The study “Total Synthesis of 3,3-Difluorinated 1-Deoxynojirimycin Analogs” focused on the synthesis and evaluation of 3,3-difluorinated analogs of 1-deoxynojirimycin (DNM). The researchers aimed to create a competitive inhibitor of α-glucosidase and α-galactosidase that could have potential applications in diabetes treatment and antiviral drugs. The synthesis involved multiple steps, starting with the allylation of glucose to obtain allyl β-D-glucopyranoside. This compound was then subjected to various reactions including benzylic methylene acetal formation, benzyl introduction, Swern oxidation, diethylaminosulfur trifluoride (DAST) treatment, and deallylation to introduce the difluoromethylene group and obtain the desired difluorinated pyranoside. Further oxidation, reductive amination, and debenzylation steps were used to obtain the final target compounds 15 and 16. The synthesized compounds were tested for their inhibitory activity against several glycosidases, among which compound 15 showed an inhibitory activity against baker's yeast α-glucosidase that was approximately 10-fold higher than that of standard miglitol. The study showed that difluorination at the C(3) position significantly enhanced the activity of the DNM analogs, making them promising candidates for further clinical studies.

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