10593-29-0Relevant articles and documents
Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis
Meguro, Yasuhiro,Noguchi, Masato,Li, Gefei,Shoda, Shin-ichiro
, (2020)
A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.
S-linked thiomimetics of phytoalexin-elicitor-active, branched oligosaccharides, their synthesis, protein-binding ability and phytoalexin- inducing activity
Ding, Yili,Contour-Galcera, Marie-Odile,Ebel, Juergen,Ortiz-Mellet, Carmen,Defaye, Jacques
, p. 1143 - 1152 (2007/10/03)
The sulfur-linked pentathiohexasaccharide 3(I),3(IV)-di-β-D- glucopyranosylthiogentiotetraose (12) has been prepared by a convergent approach involving the reaction of 1,2,4-tri-O-acetyl-6-deoxy-6-iodo-3-S- (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-β-D-glucopyranose (10) with the sodium salt of 2,3,4-tri-O-acetyl-6-S-[2,4-di-O-acetyl-3,6-di- S(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-dithio-β-D- glucopyranosyl]-1,6-dithio-β-D-glucopyranose (4). A further reaction, involving the sodium salt of the peracetylated β1-thio derivative of 12 with 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose (26), afforded the homologous sulfur-linked hexathioheptasaccharide 3(II),3(V)-di-β-D- glucopyranosylthiogentiopentaose (28). Related sulfur-linked positional isomers 3(II),3(IV)-di-D-β-glucopyranosylthiogentiotetraose (34) and 3(III),3(V)-di-β-D-glucopyranosylthiogentiopentaose (39) have been prepared using analogous synthetic strategies. Thus, S(N)2 displacement of the iodine atom in 10 by the sodium salt of 2,4-di-O-acetyl-3,6-di-S-(2,3,4,6-tetra-O- acetyl-β-D-glucopyranosyl)-1,3,6-trithio-β-D-glucopyranose afforded a tetrathiopentasaccharide, which resulted in the pentathiohexasaccharide 34 by a sequence of reactions involving the 1-thioglycose 32 in reaction with 26. The hexathioheptasaccharide 39 was obtained conveniently by the reaction of 26 with the acetylated 1-thio-6(I), 3(II), 6(II), 3(IV), 6(IV)-pentathio derivative 37, followed by deacylation. The four isomeric pentathiohexa- and hexathioheptasaccharides 12,34 and 28,39, respectively, were all found to be active in eliciting phytoalexin accumulation in soybean cotyledon tissue and in binding to a glucan-binding protein of soybean, although to a lesser extent than the corresponding O-oligosaccharides, the alternate thiohexa- and thioheptasaccharides 12,28 being more active as compared to the geminally branched isomers 34,39.
