Syntheses of oligomannosides in solution and on a soluble polymer support: a comparison.
The alpha-(1-->6)-linked and the alpha-(1-->2)-linked linear mannotetraose glycosides and, respectively, and the branched mannopentaoside [R=CH2(CH2)2CH2Cl] were synthesised by conventional methods in solution, using trichloroacetimidate donors, and the products were obtained in 39%, 42% and 40% overall yield, respectively. For comparative purposes, the same two linear tetrasaccharides were prepared by use of MPEG as a soluble polymer support, the yields being 34% and 14%, respectively. An attempted MPEG-supported synthesis of the branched pentasaccharide was unsuccessful. The merits and shortcomings of oligosaccharide syntheses on MPEG are discussed.
Blattner
Regine
R
Industrial Research Limited, PO Box 31 310, Lower Hutt, New Zealand.
Furneaux
Richard H
RH
Ludewig
Michael
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D011108:Polymers; D012996:Solutions
D009844:Oligosaccharides; D011108:Polymers; D012996:Solutions; C028569:oligomannoside; C039922:mannotetraose; D011092:Polyethylene Glycols; C028210:monomethoxypolyethylene glycol