1,6-Anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranose

1,6-Anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranose

CAS Number: 55682-48-9
Category: Fondaparinux Sodium Intermediates
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Product Specifications

CAS Number55682-48-9
Molecular FormulaC20H21N3O4
Molecular Weight367.40
Purity98%
AppearanceWhite to off-white solid
PackageFrom 100g/bottle to 25kg/drum

Product Overview

1,6-Anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranose (CAS No. 55682-48-9) is a protected monosaccharide derivative widely used as a intermediate in carbohydrate chemistry, glycosylation reactions, and the synthesis of complex oligosaccharides or glycoconjugates.

Applications

1,6-Anhydro Bridge: Rigidifies the pyranose ring system, masking both the C-1 (anomeric) hydroxyl and C-6 hydroxyl groups, which allows selective modifications at C-2, C-3, or C-4.

Azido Group (−N3) at C-2: Serves as a masked amine surrogate (easily reduced to a 2-amino group, e.g., glucosamine derivatives) or as a precursor for copper-catalyzed azide-alkyne cycloaddition.

Benzyl Protecting Groups (OBn) at C-3 and C-4: Ether-based protecting groups stable under a wide range of acidic and basic reaction conditions, cleanly removable via catalytic hydrogenolysis.

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