62778-20-5Relevant articles and documents
BRANCHED THIOCYCLOMALTO-OLIGOSACCHARIDES: SYNTHESIS AND PROPERTIES OF 6-S-α- AND 6-S-β-D-GLUCOPYRANOSYL-6-THIOCYCLOMALTOHEPTAOSE
Defaye, Jacques,Gadelle, Andree,Guiller, Alain,Darcy, Raphael,O'Sullivan, Thomas
, p. 251 - 258 (1989)
6-S-α- (2) and 6-S-β-D-glucopyranosyl-6-thiocyclomaltoheptaose (3) have been prepared by treatment of 6-O-p-tolylsulphonylcyclomaltoheptaose (1) with the sodium salts of 1-thio-α- and -β-D-glucopyranose, respectively, in 1,3-dimethyl-2-oxohexahydropyrimid
Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin
Laine, Valerie,Coste-Sarguet, Annie,Gadelle, Andree,Defaye, Jacques,Perly, Bruno,Djedaini-Pilard, Florence
, p. 1479 - 1488 (2007/10/02)
The synthesis and physico-chemical properties of branched β-cyclodextrins substituted by one or seven thioglycoside units at the primary hydroxy side are described.The solubilities in water of these compounds are strongly increased compared with the paren
Stereoselective Thioglycoside Syntheses. Part 4. A New Approach to 1,4-linked 1-Thio-disaccharides and a Synthesis of Thiomaltose
Blanc-Muesser, Michele,Defaye, Jacques,Driguez, Hugues
, p. 15 - 18 (2007/10/02)
Two approaches are devised for the preparation of thiomaltose (16).Condensation between the sodium salt of 1-thio-α-D-glucopyranose (3) and methyl 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulphonyl-α-D-galactopyranoside (5) in hexamethylphosphoramide, leads to the methyl α-thiomaltoside derivative (6).On the other hand, the displacement of the C-4 trifluoromethanesulphonate of 1,6-anhydro-D-galactopyranose diacetate (13) by the sodium salt (3) gave the 1,6-anhydro-thio-disaccharide (14).The precursor of (13), 2,3-di-O-acetyl-1,6-anhydro-β-D-galactopyranose (12) was obtained in near quantitative yield from the known 2-O-acetyl-1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose (9) by successive hydrolysis of the acetal group, orthoester formation (11), and selective opening of this intermediate through controlled acidic hydrolysis.Acetolysis of the methyl thio-maltoside (8) or the corresponding 1,6-anhydro-thio-disaccharide (14) followed by de-O-acylation afforded 4-S-α-D-glucopyranosyl-4-thio-D-glucopyranose in excellent yields. 1,2,3,6-Tetra-O-acetyl-4-S-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-4-thio-β-D-glucopyranose (15), a useful precursor of thiomaltotriosyloligosaccharides, is also prepared from the acetolysis reaction.