2,5-Dideoxy-2,5-imino-D-mannitol

Base Information

• Chemical Name: 2,5-Dideoxy-2,5-imino-D-mannitol
• CAS No.: 59920-31-9
• Molecular Formula: C6H13NO4
• Molecular Weight: 163.174
• Hs Code.: 29400090
• European Community (EC) Number: 633-130-7
• DSSTox Substance ID: DTXSID50943312
• Nikkaji Number: J265.069J
• Wikidata: Q27106325
• Pharos Ligand ID: LZGPKDPRT8B3
• Metabolomics Workbench ID: 68153
• ChEMBL ID: CHEMBL312653
• Mol file: 59920-31-9.mol

Synonyms:2,5-dihydroxymethyl-3,4-dihydroxy-pyrrolidine;2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine

Chemical Property of 2,5-Dideoxy-2,5-imino-D-mannitol

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 6.55E-08mmHg at 25°C
• Melting Point: 101-103 °C
• Refractive Index: 1.559
• Boiling Point: 395.9 °C at 760 mmHg
• Flash Point: 221.9 °C
• PSA: 92.95000
• Density: 1.408 g/cm³
• LogP: -2.63800
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 163.08445790
• Heavy Atom Count: 11
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dideoxy-2,5-imino-D-mannitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: other cyclic peptide (cyclic depsipeptide)
• Canonical SMILES: C(C1C(C(C(N1)CO)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H](N1)CO)O)O)O
• Uses: A glucosidase inhibitor A glucosidase inhibitor.

Technology Process of 2,5-Dideoxy-2,5-imino-D-mannitol

There total 83 articles about 2,5-Dideoxy-2,5-imino-D-mannitol 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%

5-azido-5-deoxy-D-fructopyranose (94801-02-2) → 2,5-dideoxy-2,5-imino-D-mannitol (59920-31-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 1292.9 Torr;

DOI:10.1021/jo00206a037

Reference yield: 100.0%

N-benzyl-3,4-di-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol (176300-12-2) → 2,5-dideoxy-2,5-imino-D-mannitol (59920-31-9)

Guidance literature:

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

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

Reference yield: 99.0%

(2R,3R,4R,5R)-2-(hydroxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine (161290-43-3) → 2,5-dideoxy-2,5-imino-D-mannitol (59920-31-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

upstream raw materials:

N-Benzhydryl-2,5-anhydro-2,5-imino-D-mannitol

5-azido-5-deoxy-D-fructopyranose

N-benzyloxycarbonyl-3-O-benzyyl-2,5-dideoxy-2,5-imino-D-mannitol

5-azido-5-deoxy-D-fructopyranose

Downstream raw materials:

(5R,6R,7R,7aR)-6,7-Dihydroxy-5-hydroxymethyl-tetrahydro-pyrrolo[1,2-c]oxazole-3-thione

(5R,6R,7R,7aR)-6,7-Dihydroxy-5-hydroxymethyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

(2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(hydroxymethyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamoylpyrrolidine

Refernces

Synthesis of regio- and stereospecifically C-deuterated derivatives of glycosidase inhibitors 1-deoxymannonojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol by intramolecular reductive amination employing deuterium gas

10.1016/S0008-6215(98)00159-1

This study focuses on the synthesis of regio- and stereospecifically C-deuterated derivatives of glycosidase inhibitors, namely 1-deoxymannonojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol, using intramolecular reductive amination with deuterium gas. The researchers employed 6-azido-1,3,4-tri-O-benzyl-6-deoxy-D-fructofuranose, obtained from 6,6'-diazido-6,6-dideoxysucrose, which was derived from sucrose. Through controlled hydrogenation with deuterium over Raney nickel, they produced 3,4,6-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-(5-H)mannitol, a partially protected derivative of 1-deoxymannonojirimycin. Further deprotection yielded 1-deoxy-(5-H)mannonojirimycin. Additionally, 2,5-dideoxy-2,5-imino-D-(5-H)mannitol was synthesized from 5-azido-5-deoxy-D-fructopyranose, and 2,5-dideoxy-2,5-imino-D-(5-H)glucitol was obtained from 5-azido-5-deoxy-L-sorbose. The study aimed to introduce deuterium as late as possible in the synthesis process to maximize its incorporation and minimize isotopic scrambling, achieving high yields and selective deuteration.