51996-13-5Relevant academic research and scientific papers
Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors
Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla
, (2020/11/10)
The knowledge of the regioselectivity between different hydroxyl groups of glycosyl acceptors is valuable in planning simple strategies for the synthesis of oligosaccharides, minimizing the use of protecting groups. With the aim of obtaining deeper knowle
Regioselectivity of glycosylation reactions of galactose acceptors: An experimental and theoretical study
Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla
, p. 2982 - 2989 (2020/01/09)
Regioselective glycosylations allow planning simpler strategies for the synthesis of oligosaccharides, and thus reducing the need of using protecting groups. With the idea of gaining further understanding of such regioselectivity, we analyzed the relative
Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates
Mancini, Ross S.,Lee, Jessica B.,Taylor, Mark S.
, p. 132 - 143 (2016/12/27)
Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functiona
Reagent-dependent regioselective control in multiple carbohydrate esterifications
Dong, Hai,Pei, Zhichao,Bystroem, Styrbjoern,Ramstroem, Olof
, p. 1499 - 1502 (2007/10/03)
(Chemical Equation Presented) Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic contr
Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates
Tsuda, Yoshisuke,Haque, Md. Ekramul,Yoshimoto, Kimihiro
, p. 1612 - 1624 (2007/10/02)
Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me-β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparaison with the results of the (Bu3Sn)2O method and direct benzoylation.The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group wich bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group.The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.
AN APPROACH TO REGIOSELECTIVE ALKYLATION OF ALKYL β-D-GALACTOPYRANOSIDES THROUGH (TRIALKYLSTANNYL)ATION
Tomoya, Ogawa,Tomoo, Nukada,Masanao, Matsui
, p. 263 - 270 (2007/10/02)
Regioselective preparation of methyl 3,6-di-O-benzyl-β-D-galactopyranoside, methyl 2,4-di-O-benzyl-β-D-galactopyranoside, and mehtyl 3,4-di-O-benzyl-β-D-galactopyranoside by the stannyl method is described.
REGIOSELECTIVE STANNYLATION. ACYLATION OF CARBOHYDRATES: COORDINATION CONTROL
Ogawa, Tomoya,Matsui, Masanao
, p. 2363 - 2370 (2007/10/02)
An efficient method for the regioselective enhancement of the nucleophilicity of polyhydroxy compounds has been developed.Partial stannylation of carbohydrate with (Bu3Sn)2O and subsequent electrophilic attack with benzoyl chloride gave rise to regioselec
