512809-21-1Relevant 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
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
, 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.
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
supporting information, 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
Gold- and Silver-Catalyzed Glycosylation with Pyranone Glycosyl Donors: An Efficient and Diastereoselective Synthesis of α-Anomers
Liu, Wenfeng,Chen, Qian,Liang, Jiashen,Du, Zhiyun,Zhang, Kun,Zheng, Xi,O'Doherty, George A.
supporting information, p. 1683 - 1686 (2015/07/20)
A mild, efficient and diastereoselective gold- and silver-catalyzed O-glycosylation with pyranone glycosyl donors is described. The reactions led to the formation of α-anomers in up to 91% yield with good diastereoselectivities.
Application of the Wharton rearrangement for the de novo synthesis of pyranosides with ido, manno, and colito stereochemistry
Cuccarese, Michael F.,Wang, Hua-Yu Leo,O'Doherty, George A.
, p. 3067 - 3075 (2013/06/27)
A de novo asymmetric synthesis of α-ido-pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)-catalyzed glycosylation in combination with a Wharton rearrangement/epoxide-opening reaction sequence to access sugars with ido, manno, and colito stereochemistry as well as several azido analogues. A de novo asymmetric synthesis of α-ido-pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)- catalyzed glycosylation in combination with a Wharton rearrangement/epoxide- opening reaction sequence to access sugars with ido, manno, and colito stereochemistry as well as several azido analogues. Copyright
De novo synthesis of deoxy sugar via a Wharton rearrangement
Wang, Hua-Yu Leo,O'Doherty, George A.
, p. 10251 - 10253 (2011/10/19)
A highly divergent synthesis of α-fuco-, α-6-deoxy-allo-, α-6-deoxy-altro-pyranosides has been achieved. This route utilizes a Wharton rearrangement as part of a new post-glycosylation transformation strategy.
Short and efficient synthetic route to methyl α-trioxacarcinoside B and anomerically activated derivatives
Magauer, Thomas,Myers, Andrew G.
supporting information; experimental part, p. 5584 - 5587 (2011/12/03)
A 9-step synthetic route to the complex carbohydrate methyl α-trioxacarcinoside B from 2-acetylfuran is described. Anomerically activated forms, including 1-phenylthio, 1-O-(4′-pentenyl), 1-fluoro, and 1-O-acetyl derivatives are also prepared.
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 asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide
Guo, Haibing,O'Doherty, George A.
, p. 5211 - 5220 (2008/12/21)
(Chemical Equation Presented) A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by
De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction
Guo, Haibing,O'Doherty, George A.
, p. 5206 - 5208 (2008/03/14)
(Chemical Equation Presented) Choose your poison: In the de novo asymmetric synthesis of the anthrax tetrasaccharide 1 (25 steps from acetylfuran), the absolute configurations of three L sugars and one D sugar were set by the Noyori reduction of acetylfuran with the S,S and the R,R reagent, respectively. The configuration of the remaining carbohydrate unit was set by highly diastereoselective palladium-catalyzed glycosylation and post-glycosylation transformations.
