111476-43-8Relevant academic research and scientific papers
Β-gluconopyranoside thiocarbonylation ester compound
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Paragraph 0069, (2016/11/14)
PROBLEM TO BE SOLVED: To provide a manufacturing method for a β-glucopyranoside thiocarbonyl ester compound. SOLUTION: The manufacturing method comprises allowing a compound of formula (I) (wherein R1is an alkyl group or an aryl
Selectivity switch in the catalytic functionalization of nonprotected carbohydrates: Selective synthesis in the presence of anomeric and structurally similar carbohydrates under mild conditions
Muramatsu, Wataru,Takemoto, Yuki
, p. 2336 - 2345 (2013/05/08)
A catalytic process for the chemo- and regioselective functionalization of nonprotected carbohydrates has been developed. This novel process allows selective thiocarbonylation, acylation, and sulfonylation of a particular hydroxy group in a particular carbohydrate in the simultaneous presence of structurally similar carbohydrates such as anomers. In addition, the chemoselectivity can be switched by regulating only the length of the alkyl chain in the organotin catalyst.
Organotin-catalyzed highly regioselective thiocarbonylation of nonprotected carbohydrates and synthesis of deoxy carbohydrates in a minimum number of steps
Muramatsu, Wataru,Tanigawa, Satoko,Takemoto, Yuki,Yoshimatsu, Hirofumi,Onomura, Osamu
supporting information; experimental part, p. 4850 - 4853 (2012/05/20)
Nonprotected carbohydrates: The catalytic regioselective thiocarbonylation of carbohydrates by using organotin dichloride under mild conditions was demonstrated. The reaction afforded various deoxy saccharides in high yields and excellent regioselectivity in a minimum number of steps. The regioselectivity of the thiocarbonylation is attributed to the intrinsic character of the carbohydrates based on the stereorelationship of their hydroxy groups (see scheme). Copyright
SELECTIVE DEOXYGENATION VIA REGIOSELECTIVE THIOACYLATION OF NON-PROTECTED GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
Haque, Ekramul Mohammed,Kikuchi, Tohru,Kanemitsu, Kimihiro,Tsuda, Yoshisuke
, p. 1016 - 1029 (2007/10/02)
Regioselective thioacylation of some non-protected glycopyranosides ( Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, Me β-D-Xyl ) was examined by the dibutyltin oxide method, using phenoxythiocarbonyl chloride as the thioacylating agent.This method gave the mono-thionocarbonates regioselectively in high yields.Acetylation of these thionocarbonates followed by deoxygenation with tributyltin hydride smoothly gave the corresponding deoxy derivatives, except for the primary thionocarbonates.Similar treatment of the pyranosides that have a cis-vicinal glycol ( Me α-D-Gal, Me β-D-Gal, Me β-L-Ara, and Ph α-L-Ara ) led to the formation of cyclic thionocarbonates, which on acetylation followed by olefination with trimethyl phosphite afforded the unsaturated derivatives in satisfactory yields.On deacetylation and subsequent hydrogenation over platinic oxide, they gave the corresponding dideoxy derivatives quantitatively.The compounds thus prepared were identified by analyses of their proton and carbon-13 nuclear magnetic resonance spectra.Keywords - glycopyranoside; regioselective thioacylation; dibutyltin oxide; deoxygenation; cis-vicinal glycol; thionocarbonate; cyclic thionocarbonate; deoxy, dideoxy sugar; unsaturated sugar; 13C-NMR
SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD
Haque, Md. Ekramul,Kikuchi, Tohoru,Kanemitsu, Kimihiro,Tsuda, Yoshisuke
, p. 430 - 433 (2007/10/02)
Treatment of non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, and Me β-D-Xyl) with dibutyltin oxide followed by thioacylation with phenoxythiocarbonyl chloride gave the mono-thionocarbonates regioselectively in high yields.Acetylation o
