1174754-28-9Relevant academic research and scientific papers
Catalytic Asymmetric Synthesis of All Possible Stereoisomers of 2,3,4,6-Tetradeoxy-4-Aminohexopyranosides
Zhu, Zhongpeng,Glazier, Daniel A.,Yang, Daoshan,Tang, Weiping
, p. 2211 - 2215 (2018)
We recently developed a divergent strategy for the synthesis of all eight possible 2,3,6-trideoxyhexopyranosides with three stereogenic centers. However, the diastereoselectivity for one of the three stereogenic centers was low and it was not controlled b
Divergent de novo synthesis of all eight stereoisomers of 2,3,6-trideoxyhexopyranosides and their oligomers
Song, Wangze,Zhao, Yu,Lynch, John C.,Kim, Hyunjin,Tang, Weiping
supporting information, p. 17475 - 17478 (2015/12/08)
All eight possible stereoisomers of 2,3,6-trideoxyhexopyranosides are prepared systematically from furan derivatives by a sequence of Achmatowicz rearrangement, Pd-catalysed glycosidation, and chiral catalyst-controlled tandem reductions. This sequence provides access to all possible stereoisomers of naturally occurring rhodinopyranosides, amicetopyranosides, disaccharide narbosine B, and other unnatural oligomeric 2,3,6-trideoxyhexopyranosides. It comprises a unique and systematic strategy for the de novo synthesis of deoxysugars.
De novo asymmetric synthesis of an α-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners
Shan, Mingde,Xing, Yalan,O'Doherty, George A.
experimental part, p. 5961 - 5966 (2009/12/08)
(Chemical Equation Presented) A highly divergent de novo asymmetric synthesis of benzyl α-6-deoxyaltropyranoside, benzyl Rascarylopyranoside, benzyl α-amicetopyranoside, and benzyl α-digitoxopyranoside has been achieved via a common pyranone intermediate. The routes rely upon a palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations. The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.
