Application of cyclic sulfates in the synthesis of 6-deoxy-D-manno-heptopyranose derivatives.
6-Deoxy-D-manno-heptopyranose was prepared in five steps starting from methyl 2,3-O-isopropylidene-alpha-D-mannopyranoside 4,6-sulfate or methyl 2,3-O-isopropylidene-alpha-D-mannofuranoside 5,6-sulfate. The glycosyl donor ethyl 2,3,4,7-tetra-O-benzoyl-6-deoxy-1-thio-alpha,beta-D-manno- heptopyranoside was used to synthesize methyl 4-O-(6-deoxy-alpha-D-manno-heptopyranosyl)-beta-D-galactopyranoside.
van der Klein
P A
PA
Gorlaeus Laboratories, Department of Chemistry, Leiden University, The Netherlands.
van Boom
J H
JH
D002240:Carbohydrate Sequence; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D004187:Disaccharides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000737:chemistry*
D003837:Deoxy Sugars; D004187:Disaccharides; D011135:Polysaccharides, Bacterial; C074756:methyl 4-O-(6-deoxy-manno-heptopyranosyl)galactopyranoside; C074750:6-deoxy-manno-heptopyranose