35674-15-8Relevant academic research and scientific papers
Visible-Light Responsive Sucrose-Containing Macrocyclic Host for Cations
Soko?owska, Patrycja,D?browa, Kajetan,Jarosz, S?awomir
supporting information, p. 2687 - 2692 (2021/04/12)
Chiral photoresponsive host 1 was prepared by a high-yield Cs2CO3-templated macrocyclization. Trans-1 transforms into long-lived cis-1 (25 days) upon irradiation with green light, and the backward transformation is triggered by blue light. Both isomers pr
Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine
Pelletier, Guillaume,Zwicker, Aaron,Allen, C. Liana,Schepartz, Alanna,Miller, Scott J.
supporting information, p. 3175 - 3182 (2016/03/19)
We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.
Microwave-assisted protocols applied to the synthesis of 1′,2,3,3′,4,4′-Hexa-O-benzylsucrose
Raposo, Cláudia D.,Petrova, Krasimira T.,Barros, M. Teresa
, p. 3027 - 3036 (2014/11/07)
The sucrose derivative 1′,2,3,3′,4,4′-hexa-O- benzylsucrose is a key intermediate for the chemoselective synthesis of various useful materials, such as macrocycles, crown ether analogs, and polymers. Several strategies for the synthesis of this compound were explored by applying microwave-assisted protocols, thus permitting significant reductions of time and energy compared to other routes. The outcomes of the different approaches were compared and the optimal one, in terms of yield and reproducibility, was found to be the initial protection at the positions 6 and 6′, with tert-butyldiphenylsilylchloride (TBDPSCl) in the presence of 4-(dimethylamino)pyridine (4-DMAP) and pyridine as a solvent, then perbenzylation of the remaining hydroxyl groups, followed by selective deprotection of the TBDPS groups to obtain the title compound.
Synthesis of 6-O-hexadecyl-and 6-O-octylsucroses and their self-assembling properties under aqueous conditions
Ohkawabata, Sachie,Kanemaru, Manami,Kuawahara, Shin-Ya,Yamamoto, Kazuya,Kadokawa, Jun-Ichi
, p. 659 - 672 (2013/01/16)
This paper reports the synthesis and self-assembling properties of 6-O-hexadecyl-and 6-O-octylsucroses. Mono-etherification of 2,3,4,1,3,4-hexa-O- benzylsucrose with the corresponding alkyl bromides predominantly took place at the glucose 6-position and t
Synthesis of phosphorylated derivatives of sucrose: 6,6′-di- phosphonate, 6- and 6′-phosphonates, and 6,6′-di-phosphine
Gawel, Anna,Jarosz, Slawomir
experimental part, p. 332 - 347 (2011/09/21)
Reaction of 6,6′dideoxy-6,6′di-iodo-1′,2,3,3′,4, 4′-hexa-O-benzylsucrose with triethyl phosphite afforded the corresponding 6,6′-diphosphonate. Selective phosphonylation either at the C-6 or 6-6′ position was also possible providing the corresponding sucrose mono-phosphonates. Reaction of 6,6′-dichloro-hexa-O-benzylsucrose with diphenylphoshine anion afforded the 6,6′-diphosphinosucrose. Copyright Taylor & Francis Group, LLC.
Crown ether analogs from sucrose
Mach, Mateusz,Jarosz, Slawomir,Listkowski, Arkadiusz
, p. 485 - 493 (2007/10/03)
A convenient synthesis of 1′,2,3,3′4,4′-hexa-O-benzylsucrose (4) from the free disaccharide is presented. Diol 4 and previously obtained 1′-O-benzyloxymethyl-2,3,3′,4,4′-penta-O-benzylsucrose (3) served as precursors for chiral crown ether analogs containing a sucrose backbone. Deprotection of macrocyclic compounds (removal of the benzyl blocks) was possible under hydrogenolysis conditions.
