18968-44-0Relevant articles and documents
Synthesis of thioglycoside analogues of maradolipid
Zeng, Xiaojun,Smith, Raymond,Zhu, Xiangming
, p. 4165 - 4170 (2013/05/23)
We describe here the first synthesis of thioglycoside analogues of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose developed recently in our laboratories. The challenging α,α- (1→1′) thioglycosidic linkage was constructed by Sch
A facile and highly stereoselective synthesis of 1-thiotrehalose
Xin, Guohong,Zhu, Xiangming
supporting information; experimental part, p. 4309 - 4312 (2012/09/22)
A facile and highly stereoselective synthesis of 1-thiotrehalose, that is, α,α-S-linked trehalose, is described. Glycosylation of configurationally pure α-glucosyl thiol 5 with glucosyl trichloroacetimidate 6 or glucosyl thioimidate 9 followed by deprotection afforded 1-thiotrehalose in excellent α-stereoselectivity and high yield. A different synthetic route to the key building block, α-glucosyl thiol 5, was also investigated in this report.
Hydrogen fluoride-mediated synthesis of 1-thiotrehaloses involving reaction of D-glucose with hydrogen sulfide
Defaye,Gadelle,Pedersen
, p. 51 - 58 (2007/10/02)
Hydrogen sulfide reacted with D-glucosde in hydrogen fluoride solution to yield preponderantly α,α-1-thiotrehalose, β,β-1-thiotrehalose, and the α,β anomer. Conditions were found under which the thiotrehaloses were obtained in the respective proportions of 8:5:5. Hydrogen sulfide reacted with D-glucose in hydrogen fluoride solution to yield preponderantly α,α-1-thiotrehalose, β,β-1-thiotrehalose and the α,β anomer. Conditions were found under which the thiotrehaloses were obtained in the respective proportions of 8:5:5.
Synthesis of Thiodisaccharides using Phase-transfer Catalysis
Chretien, Francoise,Cesare, Pierre Di,Gross, Bernard
, p. 3297 - 3300 (2007/10/02)
Synthesis of thiodisaccharides or thioglycosides was performed by phase-transfer catalysis using phosphonium or ammonium salts.Starting from glycosyl halides, reaction with Na2S gave the corresponding thiodisaccharides with inversion of configuration at the anomeric centre.With unstable glycosyl halides, a solid-liquid system was used.Unsymmetrical thiodisaccharides and 1-thioglycosides were prepared by reaction of glycosyl halides with thiolate or 1-thioglucose under p.t.c. conditions.
