82659-53-8Relevant articles and documents
Hydration index-a better parameter for explaining small molecule hydration in inhibition of ice recrystallization
Tam, Roger Y.,Ferreira, Sandra S.,Czechura, Pawel,Ben, Robert N.,Chaytor, Jennifer L.
, p. 17494 - 17501 (2008)
Several simple mono- and disaccharides have been assessed for their ability to inhibit ice recrystallization. Two carbohydrates were found to be effective recrystallization inhibitors. D-Galactose (1) was the best monosaccharide and D-melibiose (5) was the most active disaccharide. The ability of each carbohydrate to inhibit ice growth was correlated to its respective hydration number reported in the literature. A hydration number reflects the number of tightly bound water molecules to the carbohydrate and is a function of carbohydrate stereochemistry. It was discovered that using the absolute hydration number of a carbohydrate does not allow one to accurately predict its ability to inhibit ice recrystallization. Consequently, we have defined a hydration index in which the hydration number is divided by the molar volume of the carbohydrate. This new parameter not only takes into account the number of water molecules tightly bound to a carbohydrate but also the size or volume of a particular solute and ultimately the concentration of hydrated water molecules. The hydration index of both mono- and disaccharides correlates well with experimentally measured Rl activity. C-Linked derivatives of the monosaccharides appear to have Rl activity comparable to that of their O-linked saccharides but a more thorough investigation is required. The relationship between carbohydrate concentration and Rl activity was shown to be noncolligative and a 0.022 M solution of D-galactose (1) and C-linked galactose derivative (10) inhibited recrystallization as well as a 3% DMSO solution. The carbohydrates examined in this study did not possess any thermal hysteresis activity (selective depression of freezing point relative to melting point) or dynamic ice shaping. As such, we propose that they are inhibiting recrystallization at the interface between bulk water and the quasi liquid layer (a semiordered interface between ice and bulk water) by disrupting the preordering of water.
Regioselective debenzylation of C-glycosyl compounds by boron trichloride
Xie, Juan,Menand, Mickael,Valery, Jean-Marc
, p. 481 - 487 (2007/10/03)
Boron trichloride has been found to promote selective deprotection of 1,2- or 1,3-cis oriented secondary benzyl ethers of per-benzylated C-glycosyl derivatives. The reactivity towards BCl3 follows the order: C-4 ≥ C-2 > C-6 > C-3 for C-glucopyranosyl derivatives and C-3 ≥ C-4 > C-6 > C-2 for C-galactopyranosyl derivatives. Preparatively useful selective debenzylation at secondary positions was possible after careful control of reaction conditions.
