2-Deoxy-2-{[hydroxy(imino)methyl]amino}hexopyranose

Base Information

• Chemical Name: 2-Deoxy-2-{[hydroxy(imino)methyl]amino}hexopyranose
• CAS No.: 33204-32-9
• Molecular Formula: C7H14 N2 O6
• Molecular Weight: 222.198
• DSSTox Substance ID: DTXSID80954810
• Mol file: 33204-32-9.mol

Synonyms:Oprea1_737676;SCHEMBL21400726;DTXSID80954810;AKOS000520714;2-Deoxy-2-{[hydroxy(imino)methyl]amino}hexopyranose

Chemical Property of 2-Deoxy-2-{[hydroxy(imino)methyl]amino}hexopyranose

Chemical Property:

• Melting Point: 208-209 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 534.8°Cat760mmHg
• PKA: 11.51±0.70(Predicted)
• Flash Point: 277.3°C
• PSA: 146.26000
• Density: 1.65g/cm³
• LogP: -2.64070
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 222.08518617
• Heavy Atom Count: 15
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

BETA-D-GLUCOPYRANOSYLUREA 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)O)NC(=O)N)O)O)O

Technology Process of 2-Deoxy-2-{[hydroxy(imino)methyl]amino}hexopyranose

There total 21 articles about 2-Deoxy-2-{[hydroxy(imino)methyl]amino}hexopyranose 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: 64.0%

D-glucose (50-99-7) + urea (57-13-6) → β-D-glucosyl urea (33204-32-9,29315-88-6)

Guidance literature:

With ammonium chloride; at 80 ℃; for 2h; diastereoselective reaction; Neat (no solvent);

DOI:10.1039/c0gc00468e

Reference yield: 14.0%

D-Glucose (2280-44-6) + urea (57-13-6) → β-D-glucosyl urea (33204-32-9,29315-88-6)

Guidance literature:

With sulfuric acid; at 70 ℃; for 42h;

DOI:10.1016/0008-6215(89)84089-3

Reference yield:

N-(4-chlorobenzoyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)urea (1171112-63-2) → β-D-glucosyl urea (33204-32-9,29315-88-6) + N-(4-chlorobenzoyl)-N'-(β-D-glucopyranosyl)urea (1135133-67-3)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1016/j.carres.2008.01.045

upstream raw materials:

D-Glucose

urea

D-glucose

sulfuric acid

Downstream raw materials:

N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)urea

Refernces

• 1、 Somsak, Laszlo,Felfoeldi, Nora,Konya, Balint,Huese, Csaba,Telepo, Katalin,Bokor, Eva,Czifrak, Katalin. "Assessment of synthetic methods for the preparation of N-β-d-glucopyranosyl-N′-substituted ureas, -thioureas and related compounds". . p. 2083 - 2093. Retrieved 2008/12/21.