679412-07-8Relevant 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 (2018/06/14)
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
Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Lactols for de Novo Synthesis of Carbohydrate
Wang, Hao-Yuan,Yang, Ka,Yin, Dan,Liu, Can,Glazier, Daniel A.,Tang, Weiping
, p. 5272 - 5275 (2015/11/18)
The control of the stereochemistry at the anomeric position is still one of the major challenges of synthetic carbohydrate chemistry. We have developed a new strategy consisting of a chiral catalyst-directed acylation followed by a palladium-catalyzed gly
De novo asymmetric synthesis of All-d-, All-l-, and d-/l-oligosaccharides using atom-less protecting groups
Babu, Ravula Satheesh,Chen, Qian,Kang, Sang-Woo,Zhou, Maoquan,O'Doherty, George A.
supporting information; experimental part, p. 11952 - 11955 (2012/09/07)
Oligosaccharide synthesis is hindered by the need for multiple steps as well as numerous selective protections and deprotections. Herein we report a highly efficient de novo route to various oligosaccharide motifs, of use for biological and medicinal structure activity studies. The key to the overall efficiency is the judicious use of asymmetric catalysis and synthetic design. These green principles include the bidirectional use of highly stereoselective catalysis (Pd(0)-catalyzed glycosylation/post-glycosylation). In addition, the chemoselective use of C-C and C-O π-bond functionality, as atom-less protecting groups as well as an anomeric directing group (via a Pd-π-allyl), highlights the atom-economical aspects of the route to a divergent set of natural and unnatural oligosaccharides (i.e., various d-/l-diastereomers of oligosaccharides as well as deoxysugars which lack C-2 anomeric directing groups). For example, in only 12 steps, the construction of a highly branched heptasaccharide with 35 stereocenters was accomplished from an achiral acylfuran.
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.
supporting information; 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.
De Novo Synthesis of Oligosaccharades Using a Palladium-Catalyzed Glycosylation Reaction
Babu, Ravula Satheesh,Zhou, Maoquan,O'Doherty, George A.
, p. 3428 - 3429 (2007/10/03)
The natural all d- and/or unnatural all l-1,4- and 1,6-oligosaccharides were synthesized from furan alcohols using a palladium-catalyzed glycosylation reaction. The 1,4- and 1,6-α-manno-disaccharides were achieved in seven total steps starting from chiral furan alcohols. Similarly, 1,4- and 1,6-α-manno-trisaccharides were also synthesized in nine total steps. Key to the overall efficiency of this process was the use of highly diastereoselective palladium-catalyzed glycosylations, reductions, and dihydroxylations. Copyright
