816422-95-4Relevant articles and documents
Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents
Manhas, Sanjay,Taylor, Mark S.
, p. 11406 - 11417 (2017/11/10)
Protocols employing phenylboronic acid as a phase-transfer reagent for Fischer glycosidations in low-polarity organic solvents are described. In addition to providing rate acceleration, the formation of a substrate-derived boronic ester alters the course of the reaction by selective promotion of a furanoside- or pyranoside-selective pathway. Computational modeling of the relative energies of the glycoside-derived boronic esters provides results that are qualitatively consistent with the observed distributions of furanoside versus pyranoside products. The boronic esters that are obtained as direct products of these reactions serve as protected intermediates for the synthesis of functionalized glycosides. Complexation of particular diol groups by the boronic acid also enables selective transformations of mixtures of carbohydrates.
Facile synthesis of β- And α-arabinofuranosides and application to cell wall motifs of M. tuberculosis
Thadke, Shivaji A.,Mishra, Bijoyananda,Hotha, Srinivas
supporting information, p. 2466 - 2469 (2013/06/27)
Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.
Efficient synthesis of the glucosidase inhibitor blintol, the selenium analogue of the naturally occurring glycosidase inhibitor salacinol
Liu, Hui,Pinto, B. Mario
, p. 753 - 755 (2007/10/03)
(Chemical Equation Presented) An efficient synthesis of blintol, the selenium congener of the naturally occurring glycosidase inhibitor salacinol, and a potent glucosidase inhibitor itself, is described. Unlike our previously reported synthesis, this impr
Pentenyl Ribosides: New Reagents for Purine Nucleoside Synthesis
Chapeau, Marie-Christine,Marnett, Lawrence J.
, p. 7258 - 7262 (2007/10/02)
Protected pent-4-enyl ribosides and deoxyribosides were synthesized as reagents for the preparation of nucleosides and deoxynucleosides.Reaction of pent-4-enyl 2',3',5'-tri-O-benzoyl-D-erythro-pentofuranoside with five nucleobases in the presence of N-iod
