Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, get their minds active, and encourage them to do something that doesn’t involve a screen. 74808-09-6, C36H36Cl3NO6. A document type is Article, introducing its new discovery., Computed Properties of C36H36Cl3NO6
Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size
Phenyl 3,4,6-tri-O-benzyl-2-O-(3-carboxypropionyl)-1-thio-beta-D- galactopyranoside (1) was condensed via its pentafluorophenyl ester 2 with 5-aminopentyl (4a), 4-aminobutyl (4b), 3-aminopropyl (4c) and 2-aminoethyl 4,6-O-benzylidene-beta-D-glucopyranoside (4d), prepared from the corresponding N-Cbz protected glucosides 3a-d, to give the corresponding 2-[3- (alkylcarbamoyl)propionyl] tethered saccharides 5a-d. Intramolecular, ring closing glycosylation of the saccharides with NIS and TMSOTf afforded the tethered beta(1?3) linked disaccharides 6a-c, the a(1?3) linked disaccharides 7a-d and the a(1?2) linked disaccharide 8d in ratios depending upon the ring size formed during glycosylation. No beta(1?2) linked disaccharides were formed. Molecular modeling of saccharides 6-8 revealed that a strong aromatic stacking interaction between the aromatic parts of the benzyl and benzylidene protecting groups in the galactosyl and glucosyl moieties was mainly responsible for the observed regioselectivity and anomeric selectivity of the ring-closing glycosylation step.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics