Lei, Jin-Cai; Ruan, Yu-Xiong; Luo, Sheng; Yang, Jin-Song published the artcile< Stereodirecting Effect of C3-Ester Groups on the Glycosylation Stereochemistry of L-Rhamnopyranose Thioglycoside Donors: Stereoselective Synthesis of α- and β-L-Rhamnopyranosides>, Application In Synthesis of 4064-06-6, the main research area is rhamnopyranoside stereoselective synthesis ester group stereodirecting glycosylation effect.
The tuning effect of C3-ester groups on the glycosylation stereochem. of L-rhamnopyranose (L-Rha) Et thioglycoside donors is described. On one hand, the L-Rha thioglycoside donors carrying 3-O-arylcarbonyl or levulinoyl group undergo highly α-selective glycosylation to afford a wide variety of α-L-rhamnoside products in high chem. yields. On the other hand, the glycosylation of the 3-O-4-nitropicoloyl and 2-pyrazinecarbonyl group substituted L-Rha thioglycosides displays β-stereoselectivity. Only or predominant β anomeric products are obtained when these L-Rha donors couple with the primary or reactive secondary acceptors, while the β-selectivity may decrease significantly when these donors react with less reactive secondary alcs. The synthetic utility of the newly developed α- and β-directing L-Rha donors I and II has been demonstrated by the efficient synthesis of a structurally unique trisaccharide III, which is derived from the cell wall polysaccharide of Sphaerotilus natans.
European Journal of Organic Chemistry published new progress about Alkoxycarbonyl groups. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Application In Synthesis of 4064-06-6.
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