104495-07-0Relevant academic research and scientific papers
A Carbohydrate Approach to Polyol Fragments of Amphotericin and the Trienomycin- and Mycotrienin Antibiotics
Fuerstner, Alois,Baumgartner, Judith
, p. 8541 - 8560 (1993)
Hydrolytically labile ω-chloro-ω-phenylthioglycosides, obtained from the corresponding ω-phenylthioglycosides on treatment with NCS in CCl4, are readily dealkoxyhalogenated with Zn/Ag-graphite in anhydrous solvents affording enantiomerically pure synthons
Synthesis of some 6-S-heterocyclic derivatives of 1,2:3,4-Di-O-isopropylidene-α-D-galactopyranose
Martins Alho,D'Accorso,Thiel
, p. 1339 - 1343 (1996)
We applied nucleophilic substitution to 6-O-tosyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose using sulphur nucleophiles and obtained 6-S-derivatives of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. We present the physical and spectroscopic characterization of these heterocyclic compounds as well as other related compounds obtained by substitution, using other substrates. The conformational studies of all products are presented and discussed.
Synthesis of seleno-carbohydrates derived from d-galactose
Braga, Hugo C.,Wouters, Ana D.,Zerillo, Felipe B.,Lüdtke, Diogo S.
experimental part, p. 2328 - 2333 (2010/12/24)
The synthesis of seleno-galactopyranosides in a short and efficient manner is described, starting from the parent carbohydrate d-galactose. The approach described allows the synthesis of small libraries of compounds with a number of structural variations at the group attached to selenium. Compounds with aryl, propargyl, allyl, acyl, and alkyl substituents are described.
6-S-Phenyl-glycopyranosides as ready precursors to the synthesis of glycuronides
Yu, Biao,Zhu, Xiangming,Hui, Yongzheng
, p. 9403 - 9413 (2007/10/03)
6-S-Phenyl-gluco/galactopyranosides, readily prepared from the corresponding 6-hydroxy-glycosides, were demonstrated to be effective glycosyl donors or acceptors. The resulting coupling products were then easily converted into the corresponding glycuronide-containing compounds under mild conditions.
High pressure-promoted transformation of alcohols into the corresponding phenylsulfides with Bu3P-PhssPh
Kotsuki, Hiyoshizo,Matsumoto, Kazuhiko,Nishizawa, Hitoshi
, p. 4155 - 4158 (2007/10/02)
Several sterically hindered primary and secondary alcohols are efficiently converted into the corresponding phenylsulfides by using Bu3P-PhSSPh system under high pressure conditions.
Synthesis of L-gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses
Gonzalez, Francisco Santoyo,Baer, Hans H.
, p. 33 - 47 (2007/10/02)
Methyl 6-S-phenyl-6-thio-α-D-glucopyranoside, prepared in high yield from methyl α-D-glucopyranoside by the action of diphenyl sulfide and tributylphosphine in pyridine, was converted into 6-S-phenyl-6-thio-D-glucitol pentaacetate (7) by sequential hydrolysis, borohydride reduction, and acetylation.Oxidation of 7 with 3-chloroperoxybenzoic acid gave the corresponding S-epimeric sulfoxides, which underwent Pummerer rearrangement to 1-epimeric L-gulose S-phenyl monothiohemiacetal hexaacetates.Boron trifluoride-catalyzed reaction of the latter with thiophenol gave theanalogues diphenyl dithioacetal, whereas base-catalyzed methanolysis led to free L-gulose.Treatment of 7 with N-chlorosuccinimide afforded 1-epimeric 1-chloro-1-S-phenyl-1-thio-L-gulitol pentaacetates, which were hydrolyzed to provide aldehydo-L-gulose pentaacetate.The same reaction sequences were performed with 6-S-phenyl-6-thio-D-galactose, synthesized in two steps from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, furnishing ultimately L-galactose, its diphenyl dithioacetal pentaacetate, and aldehydo-L-galactose pentaacetate.Similar reaction sequences for the chain-terminal interchange of oxidation state in other ω-S-phenyl-ω-thioaldoses may prove useful for the preparation of less-common sugar derivatives.
