55682-47-8

Basic information

• Product Name: 1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-b-D-glucopyranose
• Synonyms: 1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-b-D-glucopyranose;β-D-Glucopyranose, 1,6-anhydro-2-azido-2-deoxy-4-O-(phenylMethyl)-;1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-beta-D-glucopyranose min. 99%;1,6-Anhydro-2-azido-2-deoxy-4-O-(phenylmethyl)-beta-D-glucopyranose
• CAS NO: 55682-47-8
• Molecular Formula: C₁₃H₁₅N₃O₄
• Molecular Weight: 277.2759
• Mol File: 55682-47-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-b-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-b-D-glucopyranose(55682-47-8)
• EPA Substance Registry System: 1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-b-D-glucopyranose(55682-47-8)

Safety Data

• Hazardous Substances Data: 55682-47-8(Hazardous Substances Data)

Usage

Class of compound

Carbohydrate derivative

Parent molecule

Glucose

1,6-Anhydro

Indicates the absence of a hydroxyl group at the 1 and 6 positions, forming a carbon-carbon bond instead.

2-Azido

Presence of an azide (N3) group at the 2 position.

4-O-Benzyl

A benzyl (C6H5CH2) group attached to the 4 position via an oxygen atom.

2-Deoxy

Absence of a hydroxyl group at the 2 position.

Functional groups

Azide, benzyl, and deoxy groups

Molecular complexity

High, due to the presence of multiple functional groups and structural modifications

Applications

Synthesis of complex organic molecules
Building block in chemical reactions

Potential uses

Medicinal chemistry and drug development

Reactivity

Unique, due to the presence of various functional groups that can participate in different types of chemical reactions

Solubility

Likely soluble in organic solvents, such as DMSO, methanol, or ethanol, due to its carbohydrate and benzyl group

Stability

May be sensitive to hydrolysis or other conditions that can affect the azide and benzyl groups, requiring careful handling and storage conditions.

Upstream product

• 33208-47-8 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose 
• 145240-47-7 (1R,2S,6S,7R,8R)-7-Benzyloxy-3,5,10,11-tetraoxa-4-thia-tricyclo[6.2.1.0^2,6]undecane 4,4-dioxide 
• 88261-52-3 1,6-anhydro-2-azido-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranose 
• 50767-55-0 1,6-anhydro-4-O-benzyl-2-iodo-2-deoxy-β-D-glucopyranose 
• 58871-11-7 4-O-benzyl-D-(-)-glucal 
• 3868-03-9 1,6:2,3-dianhydro-β-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 139437-39-1 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose 
• 13265-84-4 D-glucal 
• 86900-44-9 1,6-anhydro-4-O-benzyl-β-D-mannopyranose 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 104430-61-7 (R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid 
• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 
• 50604-68-7 2-acetamido-3-O-acetyl-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104875-55-0 1,6-anhydro-2-azido-4-O-benzyl-2,3-dideoxy-3-fluoro-β-D-glucopyranose 
• 107952-55-6 1,6-anhydro-2-azido-4-O-benzyl-2-desoxy-3-O--β-D-glucopyranose 
• 82739-72-8 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-trichloracetyl-β-D-glucopyranose 
• 211237-60-4 methyl 2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 359772-40-0 1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-tosyl-β-D-glucopyranose 
• 104430-62-8 1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose 
• 848850-43-1 1,6-anhydro-2-azido-4-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranose 
• 50447-92-2 2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose 
• 848850-46-4 1,6-di-O-acetyl-2-azido-4-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose 
• 42321-02-8 2-Acetamido-1,6-anhydro-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose 

Relevant articles and documents

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

Background: Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2-azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 ± 3 μM and 54 ± 5 μM, respectively). Conclusion: A complete series of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine is now accessible by 1,6-anhydrohexopyranose chemistry. Intermediate fluorinated 1,6-anhydro-2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly.

AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM

The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

SYNTHETIC PENTASACCHARIDES HAVING SHORT HALF-LIFE AND HIGH ACTIVITY

The invention concerns a pentasaccharide compound of formula (I) and the salts thereof. The invention also concerns a pharmaceutical composition comprising the synthetic pentasaccharide compound of formula (I) and its salts. The invention further concerns