85422-89-5Relevant academic research and scientific papers
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.
C -Glycosylation enabled by N -(glycosyloxy)acetamides
Li, Bo-Han,Li, Tian,Liu, Meng,Liu, Miao,Wu, Xia,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 3043 - 3046 (2020/05/08)
The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.
An Efficacious C-Glucosidation of β-Ketoesters and ketones via Enamines
Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Fiecchi, Alberto,Scala, Antonio
, p. 57 - 58 (2007/10/02)
A route for the synthesis of α-C-glucosides of β-keto esters and ketones through the reaction of the corresponding enamines with 3,3,4,6,tetra-O-benzyl-α-D-glucopyranosyl chloride activated by silver(I) trifluoromethanesulphonate is described.
The First Direct Method for C-Glucopyranosyl Derivatization of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Fiecchi, Alberto,Scala, Antonio
, p. 1245 - 1246 (2007/10/02)
Commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose, activated by trifluoroacetic anhydride reacts, in the presence of Lewis acids, with various silyl enol ethers or with allylsilane to yield C-D-glucopyranosyl derivatives of the α-configuration
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,
