53942-44-2

Basic information

• Product Name: 3,4,5,6-tetra-O-acetyl-2-(acetylamino)-2-deoxyhexose
• CAS NO: 53942-44-2
• Molecular Formula: C₁₆H₂₃NO₁₀
• Molecular Weight: 389.3545
• Mol File: 53942-44-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 481.3°C at 760 mmHg
• Flash Point: 244.9°C
• Density: 1.25g/cm³
• Vapor Pressure: 2.02E-09mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: 3,4,5,6-tetra-O-acetyl-2-(acetylamino)-2-deoxyhexose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6-tetra-O-acetyl-2-(acetylamino)-2-deoxyhexose(53942-44-2)
• EPA Substance Registry System: 3,4,5,6-tetra-O-acetyl-2-(acetylamino)-2-deoxyhexose(53942-44-2)

Safety Data

• Hazardous Substances Data: 53942-44-2(Hazardous Substances Data)

Upstream product

• 51040-52-9 2-acetamido-3,4,5,6-tetra-O-acetyl-2-deoxy-D-glucose diethyl dithioacetal 
• 6838-16-0 2-acetamido-2-deoxy-D-glucose diethyl dithioacetal 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 54220-78-9 N-[(1S,2R,3S,4R)-2,3,4,5-Tetrahydroxy-1-(methoxyimino-methyl)-pentyl]-acetamide 
• 122383-02-2 2-acetamido-2-deoxy-3,4,5,6-tetra-O-acetyl-D-glucose methyl oxime 
• 108-24-7 acetic anhydride 

Downstream Products

• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 29847-23-2 2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide 
• 246512-98-1 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranosyl azide 
• 1429306-51-3 2-acetamido-6-O-tert-butyldiphenylsilyl-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide 

Relevant articles and documents

Dichotomous Selectivity in Indium-Mediated Aza-Barbier-Type Allylation of 2-N-Acetyl Glycosyl Sulfinylimines in Brine: Convenient Access to Potent Anti-Influenza Agents

A highly diastereoselective indium-mediated allylation of 2-N-acetyl glycosyl sulfinylimines in brine under mild reaction conditions is reported. The method allows the achievement of a highly remarkable dichotomous selectivity for substrates, providing a single diastereoisomer of the product in 80-98% yield. With chiral (S)-homoallylic sulfinamide (RS)-5 and (RS)-8 formed as key intermediates, two potent anti-influenza agents, zanamivir and zanaphosphor, were synthesized in 50% and 41% overall yields, respectively.

REMOVAL OF SUGAR DITHIOACETAL GROUP WITH N-BROMOSUCCINIMIDE

Oxidative removal of the dithioacetal group of several protected sugar and 2-acylamido-2-deoxy sugar dialkyl dithioacetals with N-bromosuccinimide in 97percent aqueous acetone or 1:1 (v/v) 2-methyl-2-propanol-acetone was compared with removal with mercury dichloride-mercury(II) oxide or mercury dichloride-cadmium carbonate.In general, removal with N-bromosuccinimide proceeded more rapidly, and, with one exception, yields higher than or equal to those obtained with the method using mercury salt.