36757-11-6

Basic information

• Product Name: Methyl 2-[acetyl(methyl)amino]-3-O,4-O,6-O-trimethyl-2-deoxy-α-D-glucopyranoside
• Synonyms: Methyl 2-[acetyl(methyl)amino]-3-O,4-O,6-O-trimethyl-2-deoxy-α-D-glucopyranoside
• CAS NO: 36757-11-6
• Molecular Formula: C13H25NO6
• Molecular Weight: 291.3407
• Mol File: 36757-11-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 2-[acetyl(methyl)amino]-3-O,4-O,6-O-trimethyl-2-deoxy-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-[acetyl(methyl)amino]-3-O,4-O,6-O-trimethyl-2-deoxy-α-D-glucopyranoside(36757-11-6)
• EPA Substance Registry System: Methyl 2-[acetyl(methyl)amino]-3-O,4-O,6-O-trimethyl-2-deoxy-α-D-glucopyranoside(36757-11-6)

Safety Data

• Hazardous Substances Data: 36757-11-6(Hazardous Substances Data)

Upstream product

• 7380-60-1 methyl 2-acetamido-3,4,6-tri-O-methyl-2-deoxy-α-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 96744-17-1 Methyl 2-acetamido-2-deoxy-3,4,6-tri-O-methyl-α,β-D-glucopyranoside 
• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 

Relevant articles and documents

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ANALYSIS OF LINKAGE POSITIONS IN 2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYL RESIDUES BY THE REDUCTIVE-CLEAVAGE METHOD

The fate of methylated 2-acetamido-2-deoxy-D-glucopyranosyl residues under reductive-cleavage conditions was investigated by using methyl 2-(acetylmethylamino)-2-deoxy-3,4,6-tri-O-methyl-β-D-glucopyranoside (1), its α anomer (8), and fully methylated lacto-N-tetraitol as test compounds.Treatment of 1 with triethylsilane and trimethylsilyl trifluoromethanesulfonate in dichloromethane gave rise to (1,2-dideoxy-3,4,6-tri-O-methyl-α-D-glucopyrano)-2,3-dimethyl--2-oxazolinium trifluoromethanesulfonate.Quenching of the reaction by addition of aqueous sodium hydrogencarbonate resulted in hydrolysis of the oxazolinium salt.Compound 8 was fully stable to reductive-cleavage conditions.Thus, participation by the 2-acetamido group is necessary for glycosidic carbon-oxygen bond-cleavage to occur.Treatment of methyl 2-deoxy-2-(ethylmethylamino)-3,4,6-tri-O-methyl-α,β-D-glucopyranoside under reductive-cleavage conditions resulted in some anomerization, but neither hydrolysis nor reductive cleavage of the glycosidic carbon-oxygen bond was observed, as expected.Reductive cleavage of fully methylated lacto-N-tetraitol gave the products predicted on the basis of these and prior model studies, including 3-O-acetyl-2-(acetylmethylamino)-2-deoxy-4,6-di-O-methyl-D-glucopyranose derived from the 3-linked 2-acetamido-2-deoxy-β-D-glucopyranosyl residue.