2,5-Anhydro-2,5-imino-D-glucitol

Base Information

• Chemical Name: 2,5-Anhydro-2,5-imino-D-glucitol
• CAS No.: 132295-44-4
• Molecular Formula: C6H13NO4
• Molecular Weight: 163.174
• DSSTox Substance ID: DTXSID40437972
• Mol file: 132295-44-4.mol

Synonyms:2,5-Anhydro-2,5-imino-D-glucitol;(2S,3R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol;DTXSID40437972;MFCD06804502;AKOS030254877

Chemical Property of 2,5-Anhydro-2,5-imino-D-glucitol

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Vapor Pressure: 6.55E-08mmHg at 25°C
• Melting Point: 139-142.5 °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.: -20°C Freezer
• 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-glucitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(N1)CO)O)O)O
• Isomeric SMILES: C([C@H]1[C@H](C([C@H](N1)CO)O)O)O
• Uses: Many pyrrolidines are powerful inhibitors of glycohydrolases, enzymes responsible for cleavage of glycosidic bonds, glycoprotein processing and the gastrointestinal breakdown of dietary carbohydrates. These compounds are charged at physiological pH and are believed to associate with acidic amino acids at the active site. Inhibition of glycohydrolases could be of therapeutic value for the treatment of viral infections, cancer, diabetes, and obesity.

Technology Process of 2,5-Anhydro-2,5-imino-D-glucitol

There total 86 articles about 2,5-Anhydro-2,5-imino-D-glucitol 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%

(2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride (1609168-92-4) → 2,5-anhydro-2,5-imino-D-glucitol (132295-44-4)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; at 20 ℃; for 48h; under 3800.26 Torr;

DOI:10.1016/j.tet.2014.03.100

Reference yield: 100.0%

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine (162992-53-2) → 2,5-anhydro-2,5-imino-D-glucitol (132295-44-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 30 ℃; for 12h;

DOI:10.1016/j.tet.2005.11.037

Reference yield: 100.0%

(2S,3R,4R,5R)-N-benzyl-3,4-dibenzyloxy-5-[(benzyloxy)methyl]-2-hydroxymethyl-pyrrolidine (872360-65-1) → 2,5-anhydro-2,5-imino-D-glucitol (132295-44-4)

Guidance literature:

With hydrogenchloride; palladium dihydroxide; water; hydrogen; In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2008.10.096

upstream raw materials:

(2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol

(2S,3R,4R)-2,5-Bis-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol

5-azido-5-deoxy-L-sorbose

2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyloxy-6-O-(tert-butyldimethylsilyl)oxy-D-glucitol

Downstream raw materials:

8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-<(2-amino-6-chloropurin-9-yl)methyl>pyrrolidine