Solid-phase synthesis of thio-oligosaccharides

Angewandte Chemie - International Edition

Volumn 38, Issue 12, 1999, Pages 1782-1784

  Hummel, Gerd ^a   Hindsgaul, Ole ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Oligosaccharides; Solid phase synthesis; Thio oligosaccharides; Thioglycosides; Thiolates

Indexed keywords

OLIGOSACCHARIDE; THIOL DERIVATIVE; TRITYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033553819     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990614)38:12<1782::AID-ANIE1782>3.0.CO;2-1     Document Type: Article

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14. The resin is commercially available from Novabiochem. Immobilization was performed by using pyridine as solvent in the presence of 4-dimethylaminopyridine (DMAP) for 48 h at 60°C.
15. Yield of isolated product. The isopropylidene groups of 20, 23, 25, 27 and the O-glycosidic bonds of unprotected 22, 24, 26, 28 were partly cleaved under acidic conditions. Cleaving the benzoyl-protected thiodisaccharides from the resin afforded the corresponding disaccharides in quantitative yields since the presence of the electronegative benzoyl esters stabilizes the glycosidic linkages. The use of more acid labile linker systems is currently under investigation.