108392-13-8Relevant articles and documents
Synthesis of Symmetrical Dodeco-6,7-diuloses
Bayer, Marius,Stocker, Simon,Maichle-M?ssmer, C?cilia,Ziegler, Thomas
, p. 4347 - 4360 (2020/06/21)
Dodeco-6,7-diuloses represent a rare class of sugars and can be considered as anomerically linked di-hexoses with two hemiacetal functions in the middle. Herein, the synthesis of three symmetrical dodeco-6,7-diuloses (gluco-gluco, galacto-galacto, manno-manno) is described. For their preparation four synthetic strategies were pursued, whose mutual key step, the connection of the anomeric centers, is particularly emphasized. Specifically, C–C bond forming methods are employed, such as a Grubbs metathesis, a stannyl glycal homocoupling reaction, a coupling of a sulfinyl glycal with a sugar lactone and a Ramberg–B?cklund rearrangement. Since the ring closure via hemiacetal formation of the target compounds cannot be predicted, intensive NMR spectroscopic structure elucidation of the diuloses was performed.
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
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.