114284-07-0Relevant articles and documents
Total synthesis of candicanoside A, a rearranged cholestane disaccharide, and its 4″-O-(p-methoxybenzoate) congener
Tang, Pingping,Yu, Biao
experimental part, p. 259 - 269 (2009/06/21)
Candicanoside A (1) and its 4″-O-(p-methoxybenzoate) derivative 2 are congeners of the novel 24(23→22)abeo-cholestane glycosides that occur in the genus Ornithogalum indigenous to Southern Africa and have remarkable cytostatic activities. These two saponi
Synthesis of β-D-Glcp-(1→2)-[β-D-Ribf-(1→3)-]α-L-Rhap- (1→3)-α-L-Rhap-(1→2)-α-L-Rhap, the repeating unit of the lipopolysaccharide of Acetobacter diazotrophicus PAL 5
Zhang, Jianjun,Kong, Fanzuo
, p. 579 - 589 (2007/10/03)
A pentasaccharide, the major repeating unit of the lipopolysaccharide (LPS) of the nitrogen fixing bacterium Acetobacter diazotrophicus PAL 5 was efficiently synthesized as its allyl glycoside using a regio- and stereoselective strategy. The key acceptor, allyl 3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside (3), was prepared by selective 3-O-acetylation of allyl 4-O-benzoyl-α-L-rhamnopyranoside. Condensation of 3 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate furnished the disaccharide 5. Deallylation and subsequent trichloroacetimidation of 5 afforded 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→2)-3-O-acetyl-4-O- benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (10). Selective 3-O-glycosylation of allyl α-L-rhamnopyranoside (1) with 10 followed by benzoylation gave trisaccharide (12), which could be conveniently converted to a donor (14). Condensation of 14 with allyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside (15) gave tetrasaccharide 16. Selective deacetylation of 16 gave the acceptor 17 which was ribosylated to furnish the protected pentasaccharide, and finally deprotection led to the title compound.
Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.
Marino-Albernas,Verez-Bencomo,Gonzalez-Rodriguez,Perez-Martinez,Gonzalez-Abreu Castell,Gonzalez-Segredo
, p. 175 - 182 (2007/10/02)
The trisaccharide allyl O-(3,4-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl-al pha-L- rhamnopyranosyl)-(1----2)-3-O-methyl-alpha-L-rhamnopyranoside was synthesized from partially methylated monosaccharide derivatives. Condensation of 1,4