80441-61-8Relevant 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 diglycosylated (di)sulfides and comparative evaluation of their antiproliferative effect against tumor cell lines: A focus on the nature of sugar-recognizing mediators involved
Di Gaetano, Sonia,Bedini, Emiliano,Landolfi, Alfredo,Pedone, Emilia,Pirone, Luciano,Saviano, Michele,Traboni, Serena,Capasso, Domenica,Iadonisi, Alfonso
, (2019/07/12)
A mini-library of symmetrical and unsymmetrical diglycosyl (di)sulfides, containing D-galactose, L-fucose and N-acetyl glucosamine units, were synthesized and tested for the antiproliferative activity against cervix carcinoma (HeLa) and melanoma (A375) tumor cell lines as well as healthy fibroblasts (HDF). Comparative analysis of results seems to indicate that the most relevant antiproliferative effect is not primarily influenced by interactions with galectins, as the most cytotoxic compound observed for HeLa and A375 is not a ligand for such receptors. The most active molecules against HeLa and A375 lines also exhibited a good selectivity, showing a low toxicity to HDF cells. Obtained results offer useful indications for future design of structurally simple antitumor molecules based on sugar moieties with bridging sulfur atoms.
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.
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.
