73139-31-8Relevant articles and documents
Glycosylated eumelanin building blocks by thioglycosylation of 5,6-diacetoxyindole with an expedient selenium-based dynamic-mixture methodology
Adinolfi, Matteo,D'Ischia, Marco,Iadonisi, Alfonso,Leone, Loredana,Pezzella, Alessandro,Valerio, Silvia
scheme or table, p. 4333 - 4338 (2012/09/22)
A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding, more reactive, phenylselenenyl sulfides in the presence of diphenyl diselenide, N-bromosuccinimide (NBS) and tetrabutylammonium bromide (TBAB). An expedient thioglycosidation of 5,6-diacetoxyindole with a dynamic mixture of thioglycosides is described. Copyright
SYNTHESIS OF TWO ENANTIOMERIC TETRASUBSTITUTED CYCLOHEXANONES FROM 6-DEOXYHEX-5-ENOPYRANOSIDE DERIVATIVES
Machado, Antonio Salustiano,Olesker, Alain,Lukacs, Gabor
, p. 231 - 240 (2007/10/02)
The conversion of various 6-deoxyhex-5-enopyranoside derivatives in the presence of a catalytic amount of mercury(II) sulfate into chiral cyclohexanones has been studied.Under the experimental conditions used, the stereochemistry at position 5 of the tetr
SYNTHESE DES L-FUCOSE ET L-(3-(2)H)FUCOSE A PARTIR DU D-MANNOSE
Defaye, Jacques,Gadelle, Andree,Wong, Chuan C.
, p. 131 - 142 (2007/10/02)
Oxidation with the dimethyl sulfoxide-acetic anhydride reagent of methyl 2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside, obtained in quantitative yield from the corresponding 4,6-benzylidene acetal by stereoselective opening of a 2,3-orthoester, led in good yield to methyl 2-O-acetyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-3-ulose, which was reduced with either sodium borohydride or sodium borodeuteride into a methyl 4,6-O-benzylidene-α-D-altopyranoside or its 3-(2)H derivative.A sequence involving a C-6 halogenation-dehydrohalogenation followed by catalytic hydrogenation of the resulting methyl 6-deoxy-α-D-arabino-hex-5-enopyranoside gave methyl 6-deoxy-β-L-galactopyranoside (methyl β-L-fucopyranoside) and then α-L-fucose, with an overall yield of 24percent with respect to the starting methyl α-D-mannopyranoside.