116013-30-0Relevant academic research and scientific papers
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
Total synthesis of calicheamicin γ1I. 1. Synthesis of the oligosaccharide fragment
Groneberg,Miyazaki,Stylianides,Schulze,Stahl,Schreiner,Suzuki,Iwabuchi,Smith,Nicolaou
, p. 7593 - 7611 (2007/10/02)
The first total synthesis of the calicheamicin γ1I oligosaccharide fragment in the form of its methyl glycoside (62) has been achieved. The synthetic challenge of the B-ring was recognized and studied initially, resulting in a novel and unique solution to the stereochemical problems posed involving a [3,3]-sigmatropic rearrangement of an allylic thionoimidazolide (111). This chemistry was initially worked out on a model for the ABC-ring system (47) and then successfully applied to the real system. The success of this synthesis has enabled the completion of the first synthesis of the natural product itself, calicheamicin γ1I (1), as will be described in the following papers in this issue.
Ring Opening of 2,3-, 3,4-, and 4,6-O-Benzylidene Acetals of Pyranosides by Photobromination with Bromotrichloromethane
Chana, Jasbir S.,Collins, Peter M.,Farnia, Farnoosh,Peacock, David J.
, p. 94 - 96 (2007/10/02)
2,3-, 3,4-, and 4,6-O-Benzylidene pyranoside dervatives on photobromination in bromotrichloromethane yield bromo-deoxy-pyranoside benzoates regio- and stereo-specifically which, for the acyl derivatives of the 2,3- and 3,4- acetals, is superior to their r
CHAIN ELONGATION BY USE OF AN IRON CARBONYL REAGENT: A FACILE SYNTHESIS OF 6-DEOXYHEPTOSIDURONIC ACIDS
Baer, Hans H.,Hanna, Hanna R.
, p. 169 - 184 (2007/10/02)
A method of chain elongation at the nonreducing terminal of 6-deoxy-6-halo- and 6-O-tosyl-hexopyranosides, to give methyl (methyl 6-deoxyheptopyranosid)uronates was developed on the basis of organo-iron chemistry.Thus, methyl 2,3,4-tri-O-acetyl-6-O-p-toly
