81928-98-5Relevant academic research and scientific papers
Study of the stereoselectivity of 2-azido-2-deoxygalactosyl donors: Remote protecting group effects and temperature dependency
Kalikanda, Jane,Li, Zhitao
experimental part, p. 5207 - 5218 (2011/08/09)
The stereoselectivity of glycosylation reactions is affected by many factors. Synthesis of 1,2-cis glycosidic linkages (such as α linkages in glucose and galactose like monosaccharides) is challenging due to lack of control of the stereoselectivity. Our s
Synthesis of model ring systems related to C10-C18 analogues of the mycalamides/theopederins
Gardiner, John M.,Mills, Richard,Fessard, Thomas
, p. 1215 - 1217 (2007/10/03)
Conjugate addition to D-galactose-derived pyranones 8 and 10, with in situ enolate alkylation, or protonation, provides pyranones 11-13 or 16-19. These are related to the C10-C18 fragment of the mycalamides and provide a short entry to C10, C11, C14 and C
Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, Ssea-3, and Gb3
Bosse, Folkert,Marcaurelle, Lisa A.,Seeberger, Peter H.
, p. 6659 - 6670 (2007/10/03)
The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult α-(1→-4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the β-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the β-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.
Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks
Love, Kerry Routenberg,Andrade, Rodrigo B.,Seeberger, Peter H.
, p. 8165 - 8176 (2007/10/03)
A linear synthesis of a fully protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosyl trichloroacetimidate building blocks is reported. Envisioning an automated solid-phase synthesis of blood group determinants, the utility of glycosyl phosphates in the stepwise construction of complex oligosaccharides, such as the H-type II antigen, is demonstrated. Installation of the central glucosamine building block required the screening of a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally employed protecting groups was examined, as well as its use as a C2 stereodirecting group in glycosylations. The application of the 2-(azidomethyl)benzoyl group along with a systematic evaluation of glycosyl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that is expected to be generally amenable to the solid support synthesis of blood group determinants.
Simple oxidation of 3-O-silylated glycals: Application in deblocking 3-0-protected glycals
Kirschning, Andreas,Hary, Ulrike,Plumeier, Claus,Ries, Monika,Rose, Lars
, p. 519 - 528 (2007/10/03)
A high yielding allylic oxidation of 3-O-siIylated glycals 5-10 with the reagent system PhI(OAc)2-TMSN3 is presented. The iodine(m) species generated under these conditions is a lot more effective for generating carbohydrate-derived 3-trialkylsiloxy-2,3-d
