D-Glucose, 2-amino-2-deoxy-

Base Information

• Chemical Name: D-Glucose, 2-amino-2-deoxy-
• CAS No.: 3416-24-8
• Deprecated CAS: 2351-15-7,58-87-7,58267-75-7,880765-44-6,911653-84-4,1261161-52-7,149014-32-4,1684434-48-7
• Molecular Formula: C6H13NO5
• Molecular Weight: 179.173
• Hs Code.: 2940000000
• NCI Thesaurus Code: C83731
• RXCUI: 4845
• Mol file: 3416-24-8.mol

Synonyms:2 Amino 2 Deoxyglucose;2-Amino-2-Deoxyglucose;Dona;Dona S;Glucosamine;Glucosamine Sulfate;Hespercorbin;Sulfate, Glucosamine;Xicil

Chemical Property of D-Glucose, 2-amino-2-deoxy-

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 5.53E-10mmHg at 25°C
• Melting Point: 88oC
• Refractive Index: 1.4240 (estimate)
• Boiling Point: 449.9 °C at 760 mmHg
• PKA: pKa 8.04(H2O,t = 15.5,I=0.00,N2)(Approximate)
• Flash Point: 225.9 °C
• PSA: 124.01000
• Density: 1.563 g/cm³
• LogP: -2.71210
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 179.07937252
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

D-Glucosamine 98+% ^*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)N)O)O)O
• Isomeric SMILES: C(C1[C@@H](C(C([C@H](O1)O)N)O)O)O
• Uses: Glucosamine is an amino sugar that can regulate growth factor gene transcription. It is also widely touted as remedy for osteoarthritis (OA). Pharmaceutic aid.

Technology Process of D-Glucose, 2-amino-2-deoxy-

There total 70 articles about D-Glucose, 2-amino-2-deoxy- 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: 99.0%

D-(+)-glucosamine hydrochloride (66-84-2) → 2-amino-2-deoxyglucose (3416-24-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;

DOI:10.1515/hc-2019-0021

Reference yield: 46.3%

chitosan (deacetylation degree, 93%) + sodium acetate (127-09-3) → chitosan oligosaccharides + 2-amino-2-deoxyglucose (3416-24-8) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + Low molecular weight chitosan

Guidance literature:

With chitosanase; In water; at 40 ℃; for 20h; pH=4.5; Further Variations:; Reagents; pH-values; Product distribution; Enzymatic reaction;

DOI:10.1016/j.carres.2007.08.023

Reference yield:

3-O-[β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-[α-L-arabinopyranosyl-(1→3)]-2-acetamido-2-deoxy-β-D-glucopyranosyl]-28-O-[β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-[β-D-apiofuranosyl-(1→4)]-β-D-glucopyranosyl]oleanolic acid → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + 2-amino-2-deoxyglucose (3416-24-8) + D-glucose (50-99-7)

Guidance literature:

With water; trifluoroacetic acid; at 95 ℃; for 3h;

DOI:10.1016/j.phytol.2013.06.006

upstream raw materials:

methanol

D-Fructose

methyl 2-amino-2-deoxy-β-D-glucopyranoside

ammonia

Downstream raw materials:

2-(3-bromo-benzoylamino)-2-deoxy-D-glucose

2-hexanoylamino-2-deoxy-D-glucose

D-Mannose

L-Lactic acid

Refernces

Total synthesis of sulfated Le(x) pentaosyl ceramide

10.1016/0008-6215(94)00264-9

The research details the first total synthesis of sulfated Le" pentaosyl ceramide, a significant endeavor due to the biological importance of these compounds in cell-adhesion processes, particularly in mediating the binding of leucocytes to endothelial cells and platelets. The study aimed to provide an efficient chemical synthesis method for these ligands, which are recognized by L-selectin. The synthesis process involved a series of complex glycosylation reactions using compounds derived from D-galactose, 2-amino-2-deoxy-D-glucose, rA.tcose, and lactose, among others. Key chemicals used in the synthesis included ceramide derivative 4, glycopentaosyl donor 3, and various protecting and deprotecting agents such as levulinic anhydride, hydrazine hydrate, and NaOH. The successful synthesis was confirmed through various spectroscopic techniques, and the final products, sulfated Le" pentaosyl ceramide 1 and 2, were obtained after a series of transformations and deprotection steps. The study concluded with the achievement of a stereo-controlled synthesis of the sulfated Le" pentaosylceramides, providing a foundation for further chemical and biological scrutiny of these compounds.