84679-45-8Relevant academic research and scientific papers
A CONVERGENT TOTAL SYNTHESIS OF (-)-ANAMARINE FROM D-GLUCOSE
Lichtenthaler, Frieder W.,Lorenz, Klaus,Ma, Wei-yong
, p. 47 - 50 (1987)
The di-acetonide of 6-deoxy-aldehydo-D-glucose 12 and (S,S)-2-ethoxy-6-triphenylphosphoniomethyl-dihydropyran iodide 8 are elaborated from D-glucose each in practicable procedures of 5 and 10 steps, resp., and subsequently joined to give, after oxidation, deprotection and acetylation, (-)-anamarine (ent-1).The synthesis proves the absolute configuration of natural (+)-anamarine (1).
Synthesis of thioglycosides by tetrathiomolybdate-mediated michael additions of masked thiolates
Sridhar, Perali Ramu,Prabhu, Kandikere Ramaiah,Chandrasekaran, Srinivasan
, p. 4809 - 4815 (2007/10/03)
An efficient one-pot methodology for the synthesis of thioglycosides in excellent yields under neutral conditions through the use of benzyltriethylammonium tetrathiomolybdate [(BnNEt3) 2MoS4; 1] as a sulfur-transfer reagent has been developed. The reagent 1 reacts with sugar halides to give sugar disulfides, which then undergo reductive cleavage in situ to provide the corresponding thiolates, followed by Michael addition to give the corresponding thioglycosides. Further, the utility of this one-pot reaction in aqueous medium has been exemplified through the use of ammonium tetrathiomolybdate [(NH4)2 MoS4; 2]. The application of this methodology has been extended to the synthesis of a variety of thiosugar analogues with excellent diastereoselectivity through inter- and intramolecular reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Enantiomerically Pure Building Blocks from Sugars, 9. An Expedient Approach to Pyranoid Ene and Enol Lactones by BF3-Catalyzed Peroxidation of Glycal and Hydroxyglycal Esters
Lichtenthaler, Frieder W.,Roenninger, Stephan,Jarglis, Pan
, p. 1153 - 1162 (2007/10/02)
An effective and convenient one-pot procedure, simply involving treatment with boron trifluoride/3-chloroperbenzoic acid (MCPBA), is detailed for the high-yield acquisition of enantiomerically pure dihydropyran-2-ones from mono- and disaccharide-derived glycal and hydroxyglycal esters.An assessment of the scope of the method is given, a total of 17 examples being ample evidence for its preparative utility and apparent generality.Substantiation of the mechanism presented - BF3-promoted removal of the allylic acyloxy group, seizure by MCPBA of the allylcarboxonium ion generated, and fragmentation of the resulting hex-2-enopyranose 1-(3-chloro)perbenzoates on quenching - is provided by characterization of the perester intermediates.Conducting the reaction of glycal esters at room temperature a glycol-type C-1-C-2 bond cleavage occurs instead with the generation of acylated 4,5-dihydroxypentenals.
BORON TRIFLUORIDE-CATALYZED OXIDATION OF GLYCAL ESTERS: AN EFFECTIVE AND MILD METHOD FOR THEIR CONVERSION INTO α,β-UNSATURATED LACTONES
Jarglis, Pan,Lichtenthaler, Frieder W.
, p. 3781 - 3784 (2007/10/02)
An effective, one-step procedure for conversion of glycal and 2-acyloxyglycal esters to 2,3-unsaturated lactones has been developed, involving BF3-induced removal of the allylic acyloxy function and oxidation with m-chloroperbenzoic acid or pyridinium chl
