195625-75-3Relevant academic research and scientific papers
The stereodirecting effect of the glycosyl C5-carboxylate ester: Stereoselective synthesis of β-mannuronic acid alginates
Codée, Jeroen D. C.,Van Den Bos, Leendert J.,De Jong, Ana-Rae,Dinkelaar, Jasper,Lodder, Gerrit,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.
supporting information; scheme or table, p. 38 - 47 (2009/04/07)
(Chemical Equation Presented) Glycosylations of mannuronate ester donors proceed highly selectively to produce the 1,2-cis-linked products. We here forward a mechanistic rationale for mis counterintuitive selectivity, based on the remote stereodirecting e
Stereoselective C-glycosylation reactions of pyranoses: The conformational preference and reactions of the mannosyl cation
Lucero, Claudia G.,Woerpel
, p. 2641 - 2647 (2007/10/03)
A systematic study of C-glycosylations of acetals related to mannose and other pyranoses was conducted. The C-5 alkoxyalkyl group provides only a modest influence on stereoselectivity. On the other hand, studies of pentopyranoses bearing alkoxy groups at
Synthesis of aminocyclitols by intramolecular reductive coupling of carbohydrate derived δ- and ε-functionalized oxime ethers promoted by tributyltin hydride or samarium diiodide
Marco-Contelles, Jose,Gallego, Pilar,Rodriguez-Fernandez, Mercedes,Khiar, Noureddine,Destabel, Christine,Bernabe, Manuel,Martinez-Grau, Angeles,Chiara, Jose Luis
, p. 7397 - 7412 (2007/10/03)
The intramolecular reductive coupling of a series of simple or polyoxygenated oxime ethers δ- or ε-functionalized with bromide, α,β- unsaturated ester, aldehyde, or ketone groups is reported. The cyclization of a nitrile-tethered aldehyde is also studied. These reductive couplings are promoted by tributyltin hydride or samarium diiodide. The reactions proceed under mild conditions, in good chemical yield, and with high stereoselectivity. When applied to highly functionalized substrates derived from carbohydrates, this approach provides a selective entry to enantiomerically pure aminocyclitols of varying regio- and stereochemistry. In particular, the reductive coupling reaction of carbonyl-tethered oxime ethers promoted by samarium diiodide can be performed in a one-pot sequence, following a Swern oxidation step, allowing the direct transformation of hydroxyl-tethered oxime ethers into the corresponding aminocyclitols. Moreover, the resultant O-benzylhydroxylamine products of these cyclizations can be further reduced in situ with excess samarium diiodide, in the presence of water, to the corresponding amino alcohols in excellent yields. Some transformations of these compounds are discussed.
