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-(7-oxadecyl)-1-deoxynojirimycin

N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol

Refernces

• 1、 Behling,Farid,Medich,Scaros,Prunier,Weier,Khanna. "A short and practical synthesis of 1-deoxynojirimycin". . p. 1383 - 1386. Retrieved 1991.
• 2、 Hines, Jennifer V.,Chang, Heesun,Gerdeman, Melinda S.,Warn, Dana E.. "Isotope edited NMR studies of glycosidases: Design and synthesis of a novel glycosidase inhibitor". . p. 1255 - 1260. Retrieved 1999.
• 3、 Myeong, In-Soo,Jung, Changyoung,Kim, Ji-Yeon,Park, Seok-Hwi,Ham, Won-Hun. "Asymmetric total syntheses of (+)-2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and (?)-1-deoxymannojirimycin [(?)-DMJ] via an extended chiral 1,3-oxazine". supporting information. p. 2422 - 2425. Retrieved 2018/05/25.
• 4、 Lahav, Dani?l,Liu, Bing,Van Den Berg, Richard J.B.H.N.,Van Den Nieuwendijk, Adrianus M. C. H.,Wennekes, Tom,Ghisaidoobe, Amar T.,Breen, Imogen,Ferraz, Maria J.,Kuo, Chi-Lin,Wu, Liang,Geurink, Paul P.,Ovaa, Huib,Van Der Marel, Gijsbert A.,Van Der Stelt, Mario,Boot, Rolf G.,Davies, Gideon J.,Aerts, Johannes M. F. G.,Overkleeft, Herman S.. "A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase". supporting information. p. 14192 - 14197. Retrieved 2017/10/17.