Glucopyranosyl azide

Kobayashi and co-workers (42) reported a general synthetic pathway for the incorporation of oligosaccharides into [60]fullerene via cycloadditions between glycosyl azides and the fullerene (Scheme 9.42). The cycloaddition of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl azide 197 with [60]fullerene in refluxing chlorobenzene... 

Acetamido-4-0-(2-acetamido-3,4-di-0-acetyl-6-0-benzyl-2-deoxy-fi-D-glucopyranosyl)-3-0-acetyl-6-0-(2,3,4-tri-0-benzyl-a-L-fucopyranosyl)-2-deoxy-fl-D-glucopyranosyl Azide 32... 

S. 2,3,4-Trl-0-benzyl-6-0-f-butyldimethylsilyl-a-D-glucopyranosyi-(1-+6)-2,3,4-trl-0-benzoyl-0-D-glucopyranosyl-(1>6)-2,3,4-tri-O-benzyi-a-D-glucopyranosyl Azide (18)... 

A solution of 2,3,4-tri-O-benzyl-a-D-glucopyranosyl azide 16 (21 mg, 0.044 mmol) in 0.6 mL of dichloromethane was stirred in the presence of powdered 4-A molecular sieves and 24 mg (0.067 mmol) of Cu(OTf)2. After 10 min, a solution of 100 mg (0.067 mmol) of 3-methoxy-2-pyridyl 2,3,4-tri-O-benzyl-6-0-r-butyldimethylsilyl-a-D-glucopyranosyl-(1—>6)-2,3,4-tri-0-benzoyl-0-D-glucopyranoside 10 in 1.6 mL of dichloromethane was added dropwise over 5 h. A few drops of pyridine were added, the solvent was evaporated, and the residue was chromatographed with CCl4-acetone (10 1) as eluant to give the title compound (44 mg, 66%). 

Properties of Some 2-Amino-2-deoxy- --D glucopyranosyl Azides... 

A mino-2-deoxy-0-D-glucopyranosyl azide Cryslallization solvent Melting point, °C. [a]D, degrees Rotation temp., °C. Rotation solvent References... 

Strumpel, M K, Buschmann, J, Szilagyi, L, Gyorgydeak, Z, Synthesis and stmctural studies of anomeric 2,3,4,6-tetra-0-acetyl-5-thio-D-glucopyranosyl azides, Carbohydr. Res., 318, 91-97, 1999. 

Methoxy-2-pyridyl 2,3,4-tri-0-benzyl-6-0-tert-butyldimethylsiIyI-a-D-glucopyranosyI-(l->6)-2,3,4-tri-0-o-D-gIucopyranosyl-l(l- 6)-2,3,4-tri-0-benzoyl-p-D-glucopyranoside ci-D-Glucopyranosyl azide... 

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