Glucopyranoside methyl 2-acetamido-2-deoxy

Compound 160 was used as donor for the preparation of methyl 4,6-dideoxy-a-L-/yxo-hexopyranosyl-(l -> 3)-2-acetamido-2-deoxy-a-D-glucopyranoside, the 4 -deoxy analogue of the linkage disaccharide to the galactan chain in mycobacteria.235... 

T. Tsuchiya, K. Ajito, S. Umezawa, and A. Ikeda, Reactions on methyl 2-deoxy-2-trifluoro-acetamido-3-O-trifluoromethylsulfonyl-a-D-glucopyranoside derivatives Formation of ring-contraction compounds, Carbohydr. Res., 126 (1984) 45-60. 

Methyl 6-deoxy-2,3-0-isopropylidene-p-D-a/ o -heptofuranoside, D-155 Methyl 2-acetamido-4-0-acetyl-3,6-anhydro-2-deoxy-a-D-glucopyranoside, M-144... 

The effect of Q-alkylation on the anomeric solution equilibrium of D-glucopyranose and of methyl D-glucopyranoside has been studied. A considerable increase in the proportion of a-anomer for 2-Q-methyl-D-glucopyranose was observed, but there was no change for methyl D-glucopyranoside on Q-alkylation. A method has been reported for the preparation of all of the methyl ethers of methyl 2-acetamido-2-deoxy-a-D-glucopyranoside. Methylation of methyl (methyl o-D-mannopyranosid)uronate, methyl (methyl o-D-glucopyranosid)uronate, and methyl (methyl p-D-... 

Use of acetyl chloride in dichloromethane in the presence of 2,4,6-collidine or some other bulky base allowed selective esterification at primary sites the 5-(9-acetate 11, for example, was obtained in 91% yield from the 3,5-diol 10. Bis(2-oxo-oxazolidin-3-yl)phosphinic chloride (BOP-Cl), a new reagent for condensing alcohols and acids, has been employed in the preparation of primary esters 12. Treatment of unprotected methyl a-D-glucopyranoside, 2-acetamido-2-deoxy-D-glucose, and maltose with triphenylphosphine, DEAD, and an equimolar amount of a carboxylic acid (e.g.benzoic, methacrylic or adamantoic acid) allowed regioselective 6-0-esterifrcation (0-6 for... 

The 3-O-methyl derivative of methyl 2-acetamido-2-deoxy-/3-D-glucopyranoside has the same c.d. spectrum in water and in fluorinated alcohols. This confirms that solvent binding to the 3-hydroxyl group is important in determining the orientation of the amide relative to the 3-substituent. 

It is of interest that reaction of methyl, benzyl, and p-nitrophenyl 2-acetamido-4,6-0-benzylidene-2-deoxy-/3-D-glucopyranosides, and also the corresponding methyl a-D-glucopyranoside derivative, with ( )-2-chloropropionic acid gave, in preponderant yields, the respective 3-0-(D-l-carboxyethyl) derivatives257 only from the last-mentioned reaction was a significant amount of the 3-0-(L-l-carboxy-ethyl) derivative isolated. 

A. C. Richardson, Selective acylation of methyl 3-acetamido-3-deoxy-a-L-glucopyranoside Its conversion into the L-galacto- and L-manno-isomers, Carbohydr. Res., 4 (1967) 415421. 

Trimethylsilyl)ethyl 0-(methyl 5-acetamido-4,7,8,9 tetra-0-acetyl-3,5-dideoxy-D-glycero-a-D-ga acto-2-nonulopyranosylonate)-(2-y3)-(2,4,6-tri-0-benzoyl- fi-D-galactopyranosyl)-(l—>4 )-0-[2,3,4-tri-0 benzyl-a-i.-fiicopyranosyl-(l-y3)]-2-acetamido-6-0-benzyl-2-deoxy- -D-glucopyranoside (34)... 

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