124502-72-3Relevant academic research and scientific papers
Arylboronic acid-mediated glycosylation of 1,2-dihydroxyglucoses
Izumi, Sanae,Kobayashi, Yusuke,Takemoto, Yoshiji
, p. 350 - 362 (2019/07/31)
- We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cJi-a-D-glucopyranosides.
Epoxidation-alcoholysis of cyclic enol ethers catalyzed by Ti(O iPr)4 or Venturello's peroxophosphotungstate complex
Levecque, Pieter,Gammon, David,Kinfe, Henok Hadgu,Jacobs, Pierre,De Vos, Dirk,Sels, Bert
, p. 1800 - 1806 (2008/02/10)
Venturello's peroxophosphotungstate compound and Ti(OiPr) 4 were successfully used as catalysts for the epoxidation-alcoholysis of various dihydropyrans and dihydrofuran using H2O2 as the oxidant. Different alcohols can be used as solvents and nucleophiles, resulting in hydroxy ether products with varying alkoxy groups. The Venturello compound can also be used as catalyst in a biphasic conversion of dihydropyran, in which long chain alcohols or fatty acids are incorporated in the hydroxy ether products with high yield and (stereo)selectivity. This journal is The Royal Society of Chemistry.
Synthesis of mono- and dihydroxylated furanoses, pyranoses, and an oxepanose for the preparation of natural product analogue libraries
Yu, Xiao Ming,Han, Huijong,Blagg, Brian S. J.
, p. 5599 - 5605 (2007/10/03)
Numerous biologically active natural products contain furanoses and pyranoses with mono- and dihydroxylated substituents. However, much of the structure-activity studies on such molecules is gathered on the aglycons without attention to the corresponding carbohydrate components. Consequently, there are few synthetic procedures that enable the rapid preparation of mono- and dihydroxyfuranoses and mono- and dihydroxypyranoses and no report for a 3,4-dihydroxyoxepanose. In this article we report the practical synthesis of orthogonally protected five-, six-, and seven-membered carbohydrate derivatives. The succinct manner in which these molecules were synthesized allows the rapid preparation of analogues aimed at discovering the role of ring size and individual hydroxyl moieties on the pyranose skeleton.
Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 15: Regioselectivity of the opening reactions with MeOH of remote O-substituted regio- and diastereoisomeric pyranosidic epoxides under condensed- and gas-phase operating conditions
Crotti, Paolo,Renzi, Gabriele,Favero, Lucilla,Roselli, Graziella,Di Bussolo, Valeria,Caselli, Micaela
, p. 1453 - 1467 (2007/10/03)
The regiochemical behavior of pairs of regio- and diastereoisomeric epoxides derived from the 3,4,5,6-tetrahydro-2H-pyrane system, bearing an acetal group as the remote functionality, was determined in the acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D3+), as the promoting agent. With only one exception, the results obtained in the opening process of these epoxides indicate the incursion in the gas-phase of D+-mediated chelated bidentate species able to modify the regiochemical result found in the methanolysis in the cd-phase.
Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans-oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran
Calvani, Federico,Crotti, Paolo,Gardelli, Cristina,Pineschi, Mauro
, p. 12999 - 13022 (2007/10/02)
The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalization through chelation processes assisted by metal ions, was verified in cyclic oxirane systems having the polar functionality in an allylic position to the oxirane ring. The diastereoisomeric cis/trans epoxide pairs 5,6 and 7,8 derived from 3-benzyloxycyclohexene, and 2-benzyloxy-5,6-dihydro-2H-pyran, respectively, were prepared and several of their opening reactions were studied. The regioselectivity observed largely depends on the reaction conditions (standard or metal-assisted) and, interestingly, on the nature of the nucleophile used.
Stereoselective template-directed C-glycosidation. Silver(I)-mediated intramolecular reactions of (2-pyridylthio)glycosidic silyl enol ethers
Craig,Munasinghe
, p. 663 - 666 (2007/10/02)
The synthesis and highly stereoselective intramolecular cyclization reactions of a series of (2-pyridylthio)glycosides possessing silyl enol ether-containing appended groups are described. The cyclizations are explained in terms of S(N)1-like reactions proceeding via anomeric cationic species.
Regiospecific Enolates from Tetrahydropyran-3-one. Synthetic Equivalents of a Thermodynamically and Kinetically Disfavoured Enolate Isomer
Cox, Paul,Lister, Simon,Gallagher, Timothy
, p. 3151 - 3157 (2007/10/02)
Two synthetic equivalents of the tetrahydropyran-3-one enolate 3 are described.Lithiation of the methoxy enol ether 8b provides the β-lithiated enol ether 10 and although this species does serve as an equivalent of the enolate 3, its use is limited by the
REGIOSPECIFIC TETRAHYDROPYRAN-3-ONE ENOLATES. SYNTHESIS AND REACTIVITY OF SILYL ENOL ETHER DERIVATIVES
Cox, Paul,Mahon, Mary F,Molloy, Kieran C,Lister, Simon,Gallagher, Timothy
, p. 2437 - 2440 (2007/10/02)
The synthesis and reactivity of silyl enol ether (3) is reported.This reagent complements the reactivity of the lithiated enol ether (2) previously used as a synthetic equivalent of the regiospecific tetrahydropyran-3-one enolate (1).
