116087-65-1Relevant articles and documents
Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification
Delbrouck, Julien A.,Bochatay, Valentin N.,Tikad, Abdellatif,Vincent, Stéphane P.
supporting information, p. 5562 - 5566 (2019/08/01)
A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.
Synthesis of sialic acid derivatives based on chiral substrate-controlled stereoselective aldol reactions using pyruvic acid oxabicyclo[2.2.2]octyl orthoester
Norimura, Yusuke,Yamamoto, Daisuke,Makino, Kazuishi
supporting information, p. 640 - 648 (2017/01/25)
The synthesis of sialic acids and their analogs was accomplished based on substrate-controlled asymmetric aldol reactions between sterically complicated aldehydes easily prepared from commercially available carbohydrates and a novel pyruvic acid oxabicyclo[2.2.2]octyl orthoester. Systematic aldol reaction studies using chiral aldehydes revealed that α,β,γ-benzyloxy-substituted aldehydes with an α,β-anti relative configuration preferentially provided the Felkin products with the 4,5-anti configuration with high diastereoselectivity. The relative β,γ-configuration in α,β,γ-benzyloxy-substituted aldehydes with an α,β-syn arrangement exerted a secondary effect on the diastereoselectivity of the stereogenic center formed in aldol reactions, and α,β-syn-β,γ-anti benzyloxyaldehyde exhibited superior diastereoselectivity to α,β-syn-β,γ-syn benzyloxyaldehyde to yield the Felkin products.
The asymmetric epoxidation of divinyl carbinols: Theory and applications
Smith, David B.,Wang, Zhaoyin,Schreiber, Stuart L.
, p. 4793 - 4808 (2007/10/02)
The asymmetric epoxidation of symmetric divinyl carbinols is illustrative of a reaction process that combines an initial asymmetric synthesis with a subsequent kinetic resolution to provide products with extraordinary levels of enantiomeric purity. The application of this process to the asymmetric synthesis of natural products is presented herein.
