Mannose azide derivative

Nucleophilic Displacement Reactions in Carbohydrates. Part XI. Reaction of Methyl 6-Deoxy-2,3-O-isopropylidene-4-O-methyl-sulphonyl-a-L-talopyranoside with Sodium Azide A Synthesis of L-Perosamine (4-Amino-4,6-dideoxy-L-mannose) Derivatives, J. S. Brimacombe, O. A. Ching, and M. Stacey, J. Chem. Soc. C, (1969) 1270-1274. 

Treat and grow cells in the presence of 20 pM Ac4ManNAz for at least 3 days. The azide-mannose derivative may be solubilized in 70 percent DMSO as a more concentrated stock solution and then an aliquot added to the media containing the cells. Alternatively, mice may be treated with the azide-sugar derivative in aqueous DMSO at a level of 100-300 mg/kg, using an injection of 200 pi administered intraperitoneally daily for 7 days. 

Alternatively, methyl 6-0-benzoyl-2,3-0-isopropylidene-a-D-talopyranoside (57), derived from D-mannose, was utilized for the synthesis of swainsonine but in low yield (Scheme 6)P Mesylation of 57 followed by removal of the isopropylidene group with TEA, displacement of the mesylate group with azide ion, acetonation with DMP in acetone and... 

The 2-acetamido derivative of DNJ (35) has been prepared by reaction of azide followed by reduction and acetylation of the corresponding 2,3-anhydro-o-mannose derivative. Compound 35 was incorporated into oligosaccharide mimics of sialyl Le and sialyl Le, ... 

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-... 

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