Glucopyranoses, 2-azido-2-deoxy

Seven-membered heterocycles containing one nitrogen atom may be obtained either from 105 (see p. 376) or 6-amino-6-deoxy-D-glucose (227) by reduction122 to 228, or from 6-azido-6-deoxy-D-glucopyranose (229) by oxidation to 230 followed by reduction of 230 to 231. A... 

D. Tailler, J. C. Jacquinet, A. M. Noirot, and J. M. Beau, An expeditious and stereocontrolled preparation of 2-azido-2-deoxy-P-D-glucopyranose derivatives from D-glucal, J. Chem. Soc. Perkin Trans. /(1992) 3163-3164. 

M. Kloosterman, M. P. de Nijs, and J. H. van Boom, Synthesis of l,6-anhydro-2-0-trifluoromethanesulphonyl-/l-D-mannopyranose derivatives and their conversion into the corresponding l,6-anhydro-2-azido-2-deoxy-/ -D-glucopyranoses a convenient and efficient approach, J. Carbohydr. Chem., 5 (1986) 215-233 compare Ref. 129. 

Institut of Physical and Chemical Research, 3-Azido-l,6-anhydro-3-deoxy-2,4-di-0-benzyl-/l-D-glucopyranose, Japan Kokai Tokkyo Koho JP 57181094 Chem. Abstr., 98 (1983) 126566. 

V. Pavliak and P. Kovac, A short synthesis of l,3,4,6-tetra-0-acetyl-2-azido-2-deoxy-P-D-glucopyranose and the corresponding a-glucosyl chloride from D-mannose, Carbohydr. Res., 210 (1991) 333-337. 

C -Acetyl-2-azido-3,4-di-0-benzyl-2-deoxy-j3-D-glucopyranosyl chloride reacts with 2,3,4,6-tetra-0-benzyl-o -D-glucopyranose or 2,3,4,6-tetra-O-acetyl-a-D-mannopyranose with good stereoselectivity to yield Q ,a-trehalosamine or 0 ,a-mannotrehalosamine (Scheme 2) Several other 0 ,tt-(l l)-linked disaccharides of the trehalosamine type and containing additional azido-groups were also synthesized. 

Sulphonate displacement reactions have been used to introduce nitrogen functionality. 2-Amino-2-deoxy-D-arabinose has been synthesized in two related nine-step procedures from methyl 3, - -Isopropylldene-D-arablnopyranoside, involving reaction of a 2- -tosyl-D-rlboside with either azide ion or hydrazine. A variety of 1,6-anhydro-2-azido-2-deoxy-6-D-glucopyranose derivatives, of potential as glucosamine monomers in oligosaccharide synthesis, have been obtained from the corresponding 1,6-anhydro-D-mannose 2-trl-... 

Preparation of di-l,6-0-acetyl-2-azido-3-0-benzyl-2-deoxy-4-0-(2-0-acetyl-3-0-benzyl-4-0-/ ara-methoxybenzyl-6-0-f r -butyl-dimethylsilyl-a-L-idopyranosyl)-D-glucopyranose. 

Di-l,6-(9-acetyl-2-azido-3-(9-benzyl-2-deoxy-4-(9-(2-(9-acetyl-3-(9-benzyl-6-0-ferf-butyldimethylsilyl-a-L-idopyranosyl)-D-glucopyranose (720 mg, 0.91 mmol)... 

Benzyl 1,6-Anhydro-2-azido-3-0-benzyl-2-deoxy-p-D-glucopyranose [55682-57-0]... 

Dibenzyl l,6-Anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-P-D-glucopyranose [67227-89-8]... 

The photoaffinity labelling compound 6-(4-azido-2-hydroxy-benzamido)-6-deoxy-D-glucopyranose, and its D-galacto-isomer, have been synthesized both by acylation of suitable 0-protected amino-... 

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