Angles d’Ortoli, Thibault’s team published research in Journal of Organic Chemistry in 82 | CAS: 4972-31-0

Angles d’Ortoli, Thibault published the artcileStructure-Reactivity Relationships of Conformationally Armed Disaccharide Donors and Their Use in the Synthesis of a Hexasaccharide Related to the Capsular Polysaccharide from Streptococcus pneumoniae Type 37, Product Details of C11H15NOS, the publication is Journal of Organic Chemistry (2017), 82(15), 8123-8140, database is CAplus and MEDLINE.

To advance the field of glycobiol., efficient synthesis methods of oligosaccharides and glycoconjugates are a requisite. In glycosylation reactions using super-armed donors, both selectivity and reactivity issues must be considered, and we herein investigate these aspects for differently protected β-linked 2-O-glycosylated glucosyl donors carrying bulky tert-butyldimethylsilyl groups to different extents. The acceptors in reactions being secondary alcs. presents a challenging situation with respect to steric crowding. Conformational pyranose ring equilibrium of the super-armed disaccharide donors with axial-rich substituents contained skew and boat conformations, and three-state models were generally assumed. With NIS/TfOH as the promotor, 2,6-di-tert-butyl-4-methylpyridine as the base, and a dichloromethane/toluene solvent mixture, Et 1-thio-β-D-glucosyl disaccharide donors having 6-O-benzyl group(s) besides tert-butyldimethylsilyl groups were efficiently coupled at -40 °C to the hydroxyl group at position 3 of glucopyranosyl acceptors to form β-(1â†?),β-(1â†?)-linked trisaccharides, isolated in excellent 95% yield. The more axial-rich donors in skew and boat conformations are thus pre-organized closer to the assumed transition state in these glycosylation reactions. The developed methodol. was subsequently applied in the synthesis of a multi-branched hexasaccharide related to the capsular polysaccharide from Streptococcus pneumoniae type 37, which consists of a β-(1â†?)-linked backbone and a β-(1â†?)-linked side chain of D-glucosyl residues in disaccharide repeating units.

Journal of Organic Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Product Details of C11H15NOS.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem