85422-87-3Relevant 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.
Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation
Bennett, Clay S.,Ling, Jesse
, p. 4304 - 4308 (2020/02/11)
C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results i
The mukaiyama type aldol reaction for the synthesis of: Trans-2,6-disubstituted tetrahydropyrans: Synthesis of diospongin a and b
Bharath, Yada,Choudhury, Utkal Mani,Sadhana,Mohapatra, Debendra K.
, p. 9169 - 9181 (2019/11/05)
An efficient synthesis protocol for the preparation of trans-2,6-disubstituted tetrahydropyrans by the reaction of 1-phenyl-1-triemthylsiloxyethylene with six membered cyclic hemiacetals in the presence of iodine is developed. This reaction proceeds smoothly under mild conditions employing a catalytic amount of molecular iodine. The feature of this novel conversion includes milder reaction conditions, broader substrate scope, functional group tolerance and good diastereoselectivity. The efficiency and practicality of the current method were successfully displayed in the total synthesis of diospongin A and B in good yields.
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,
C-GLYCOSIDATION OF PYRIDYL THIOGLYCOSIDES
Williams, Robert M.,Stewart, Andrew O.
, p. 2715 - 2718 (2007/10/02)
The pyridylthioglycosides 1 are efficiently transformed into the corresponding C-glycosides via reaction with silver(I) triflate and a variety of carbon nucleophiles.
