99701-77-6Relevant academic research and scientific papers
An Improved Method for the Synthesis of Anomerically Allylated C-Glycopyranosides and C-glycofuranosides.
Kozikowski, Alan P.,Sorgi, Kirk L.,Wang, B. C.,Xu, Zhang-bao
, p. 1563 - 1566 (1983)
An improved procedure for the anomeric C-allylation of several carbohydrate derivatives is described.
Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group
Tang, Weiping,Ye, Wenjing,Stevens, Christopher M.,Wen, Peng,Simmons, Christopher J.
, p. 16218 - 16225 (2021/01/19)
C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.
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
Control of α/β stereoselectivity in lewis acid promoted C-glycosidations using a controlling anomeric effect based on the conformational restriction strategy
Tamura, Satoru,Abe, Hiroshi,Matsuda, Akira,Shuto, Satoshi
, p. 1021 - 1023 (2007/10/03)
The kinetic anomeric effect has been used to control both α and β stereoselectivity in glycosidation reactions. Depending on the restricted conformation 4C1 or 1C4 of the substrate, the anomeric a (1→2) or β product (3zb4) was obtained highly stereoselectively from the Lewis acid promoted anomeric allylation with allyltrimethylsilane (TIPS=triisopropylsilyl).
O-Glycosyl Imidates, 19. - Reactions of Glycosyl Trichloroacetimidates with Silylated C-Nucleophiles
Hoffmann, Michael G.,Schmidt, Richard R.
, p. 2403 - 2419 (2007/10/02)
Reaction of O-benzyl-protected α-glycopyranosyl trichloroacetimidates 1 and the xylo analogues 7 with silyl enol ethers or allyltrimethylsilane as C-nucleophiles yields with zink chloride as catalyst mainly or exclusively α-C-glycosides (5a-α to 5h-α, 8b,
