2-Deoxy-2-acetamido-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride, CAS No. 3068-34-6

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3068-34-6

Catalog No. EBD106009

CAS 3068-34-6

Name 2-Deoxy-2-acetamido-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride

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Basic Information

Synonyms: 2-acetamido-2-deoxy-alpha-D-glucopyranosylchlor 2-Acetamido-2-Deoxy-Alpha-D-GlucopyranosylChloride3,4,6-Triacetate 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosylchloride 2-Deoxy-2-acetamido-3,4,6-tri-O-acetyl-α-D-glucopyranosylchloride

Molecular Formula: C14H20ClNO8

Molecular Weight: 365.76

MDL Number: MFCD00069776

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides

Product Description:

2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride is a key protected glycosyl donor derivative of N-acetylglucosamine (GlcNAc). It features a reactive anomeric chloride leaving group and acetyl protecting groups on the hydroxyls, making it a versatile intermediate for the stereoselective synthesis of β-linked oligosaccharides and glycoconjugates via glycosylation reactions. Its primary application is in the chemical and chemoenzymatic synthesis of complex carbohydrates, glycopeptides, and glycolipids. These molecules are crucial for research in glycobiology, the development of carbohydrate-based vaccines, and the study of cell-surface recognition processes. The compound serves as a fundamental building block for constructing N-acetylglucosamine-containing structures found in biological systems. This reagent is moisture-sensitive and typically requires handling under anhydrous conditions. It is a standard tool in synthetic carbohydrate chemistry laboratories for the preparation of biologically relevant glycan structures and their analogs.

Physical Properties

Melting Point: >214 °C (dec.)(lit.)

Boiling Point: 516.4 °C at 760 mmHg

Flash Point: 266.1 °C

Density: 1.32 g/cm3

Refractivity: 117.5 ° (C=1, CHCl3)

Storage: −20°C