Modification of methyl O-propargyl-D-glucosides: model studies for the synthesis of alkynyl based functional polysaccharides.
Methyl 4,6-O-benzylidene-2,3-di-O-propargyl-alpha-D-glucoside (2) has been prepared and its structure determined, including its X-ray structural analysis. For comparison the structure of the corresponding allyl derivative has also been determined by X-ray crystallography. Glucoside 2 is a versatile starting material for numerous novel derivatives such as diols, a diester, a diacid, and a dialdehyde. Subjecting 2 to a Mannich reaction leads to a (bis)amine in excellent yields. The click reaction between 2 and benzyl azide furnishes a (bis)triazole as the main product. Deprotection of 2 furnishes a (bis)propargyl ether, which can be converted by the methodology developed for 2 to the corresponding (bis)acetylenes; click reaction with benzyl azide converts 2 into a (bis)triazole.
Tankam
Pascal F
PF
Technical University Braunschweig, Institute of Organic Chemistry, Hagenring 30, D-38106 Braunschweig, Germany.
Mischnick
Petra
P
Hopf
Henning
H
Jones
Peter G
PG
D000480:Alkynes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008757:Methylglucosides / Q000737:chemistry*; D015394:Molecular Structure; D011134:Polysaccharides / Q000138:chemical synthesis*
D000480:Alkynes; D008757:Methylglucosides; D011134:Polysaccharides