1,6-Di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose Fondaparinux Intermediate CAS 55682-49-0 NT

1,6-Di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose (CAS 55682-49-0) is a protected glucose derivative featuring an azide functionality at the C-2 position and benzyl ether protecting groups at the C-3 and C-4 positions . This compound is also identified as Fondaparinux Sodium Intermediate 2, a key building block in the synthesis of the anticoagulant drug Fondaparinux Sodium .

Chemical Characteristics:

• Contains a glucopyranose ring with α-anomeric configuration

• Features an azido group at C-2, which serves as a precursor for the amino group in glycosaminoglycan synthesis

• Protected with benzyl groups at C-3 and C-4, and acetyl groups at C-1 and C-6

• Molecular weight: 469.49 g/mol 

• Melting point: 95-96°C 

Key Role in Fondaparinux Synthesis:

Fondaparinux Sodium is a synthetic pentasaccharide anticoagulant that selectively inhibits factor Xa. This compound serves as a critical glucose building block in the multi-step synthesis of the drug, contributing to the formation of the glucosamine core structure. The azide functionality is later reduced to the amine, while the protecting groups are sequentially removed to yield the final active pharmaceutical ingredient .

Applications:

• Pharmaceutical Manufacturing: As a key intermediate in the commercial synthesis of Fondaparinux Sodium API

• Carbohydrate Chemistry: Used as a glycosylation donor for constructing complex oligosaccharides

• Analytical R&D: Serves as a reference standard for quality control (QC) and analytical method development

• Anticoagulant Research: Suitable for studies on factor Xa inhibitors and heparin-related compounds

Packaging: ___ (e.g.: 1g, 5g, 10g per package, as per customer's request)

Storage: Store in a cool, dry, well-ventilated area, away from direct sunlight and moisture. Recommended storage temperature: 2-8°C (Refrigerator) for long-term storage

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