O¹,O²:O³,O⁵-Bis(phenylboranediyl)-α-D-glucofuranose

Abstract

The title compound, C18H18B2O6, was formed by the reaction between phenyl­boronic acid and d‐glucose. The structure is analogous to those of d‐glucoboronates previously prepared and characterized by NMR. In the crystal structure, mol­ecules are linked into one‐dimensional chains along [100] via O—H⋯O hydrogen bonds [O⋯O = 2.8283 (17) Å].

Analysis of the relative stability of trigonal and tetrahedral boronate cyclic esters in terms of boronic acid and diol acidities and the strain release effect

“…[12] Recently, the K a E /K a B ratio was interpreted in terms of some electronic effects on basis of theoretical calculations. [8c] Available structural data show that for 1,2-diols, the O-B-O angles in trigonal esters are around 113 , [13][14][15][16] sufficiently small to create a considerable strain and for 1,3-diols these angles are about 123 , [13][14][15] quite close to the normal sp 2 angle. The results for tetrahedral hydroxyboronates are limited by catechol esters [17][18][19] with O-B-O angles about 102 , whereas in the trigonal catechol ester of PBA, the O-B-O angle is 109.8 .…”

Stable complex formation with boric acid in pyrolysis of levoglucosan in acidic media

“…Ester formation is a characteristic reaction between sugars and boric acid or boronic acid in nonaqueous media [12][13][14][15][16] and in alkaline aqueous solution [12,[17][18][19][20][21]. In particular, 1,2-and 1,3-cis-diols in sugars form comparatively stable five-and six-membered cyclic esters, with the release of water.…”

One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice

“…Both servers predicted no violation of the Lipinski rule of 5 for the two compounds. 8); O1-C6, 1.436(7); O2-B2, 1.371(7); O2-C7, 1.449(7); O3-B1, 1.353(8); O3-C13, 1.448(7); O5-B2, 1.369(8); O5-C15, 1.434 (7). Selected bond angles (°): O3-B1-O1, 112.6(5); O5-B2-O2, 112.5 (5).…”

“…Furthermore, synthetic procedures carried out to form diol–boronic adducts have been explored. In this sense, several adducts derived from phenylboronic acid and carbohydrates, as well as crystals derived from β-fructopyranose [ 6 ], α- d -glucofuranose [ 7 ], and β- d -arabinopyranose [ 8 ], have been reported. The formation of these adducts is interesting, among other reasons, because of the disposition of different hydroxyl groups with the feasibility of reaction.…”