[1,6-anhydro-N-acetyl-beta-D-glucosamines in synthesis of oligosaccharides. I. Synthesis of 3-acetate and 3-benzoate of 1,6-anhydro-N-acetyl-beta-D-glucosamine through a 4-O-trityl derivative].
3-O-Acetyl and 3-O-benzoyl derivatives of 1,6-anhydro-N-acetyl-beta-D-glucosamine were synthesized via its selective tritylation followed by the 3-O-acylation and removal of the trityl protective group. Tritylium trifluoromethanesulfonate, which can easily be prepared by mixing solutions of triphenylcarbinol and trimethylsilyl trifluoromethanesulfonate in an equimolar ratio, was suggested as a reagent for the effective tritylation of a secondary hydroxyl group.
Tyrtysh
T V
TV
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia.
Baĭramova
N E
NE
Bovin
N V
NV
D000085:Acetates / Q000737:chemistry*; D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
C412224:1,6-anhydro-N-acetylglucosamine; D000085:Acetates; D001565:Benzoates; D007202:Indicators and Reagents; D009844:Oligosaccharides; D000117:Acetylglucosamine