17317-98-5Relevant academic research and scientific papers
Synthesis of thioglycoside analogues of maradolipid
Zeng, Xiaojun,Smith, Raymond,Zhu, Xiangming
, p. 4165 - 4170 (2013)
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
An Expeditious Synthesis of 1-Thiotrehalose
Tardieu, Damien,Céspedes Dávila, Maria F.,Hazelard, Damien,Compain, Philippe
, p. 3927 - 3930 (2018/07/21)
A two-step synthesis of 1-thiotrehalose is reported. In the key TMSOTf-mediated double thioglycosylation step, the tri- O -benzyl 1,6-anhydro-D-glucose reactant behaves both as a glycosyl donor and a glycosyl acceptor precursor. In this highly convergent process, two carbon-sulfur bonds are created at the anomeric positions with a high level of stereocontrol.
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.
