135192-39-1Relevant academic research and scientific papers
Tunable stereoselectivity in the synthesis of α- and β-aryl glycosides using 1,2-α-anhydrosugars as glycosyl donors
Somasundaram, Devaraj,Balasubramanian, Kalpattu K.,Bhagavathy, Shanmugasundaram
, p. 95 - 102 (2017)
The stereochemical course of O-glycosidation of 1,2-α-D-anhydrosugars (glycal epoxides) with phenols can be tuned by varying the metal ion of the base. While the reaction of 1,2-α-D-anhydrosugars with phenols mediated by trimethylaluminium leads exclusive
Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions
Somasundaram, Devaraj,Balasubramanain, Kalpattu K.,Shanmugasundaram, Bhagavathy
supporting information, p. 764 - 767 (2019/02/16)
The ring opening of α-D-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-t
KOtBu-mediated aromatic O-glycosylation of 1,2-anhydrosugar and aryl boronic acid
Liu, Chen-Fu,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 1372 - 1374 (2018/03/29)
A new approach for the synthesis of phenolic glycosides via aromatic O-glycosylation of 1,2-anhydrosugar and aryl boronic acids was disclosed. This method is characterized by the use of aryl boronic acid as the aryl source and produces phenolic glycosides
Synthesis of a phenyl β-avobioside derivative of the disaccharide component of avoparcins
Dong,Tillequin,Monneret,Horvath,Sztaricskai
, p. 107 - 115 (2007/10/02)
The synthesis of the phenyl β-glycoside of avobiose, a disaccharide fragment present in the antibiotic avoparcin, is reported. It is based on glycosylation of phenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside with 2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoro
Stereospecific synthesis of aryl β-glucosides: An application to the synthesis of a prototype corresponding to the aryloxy carbohydrate domain of vancomycin
Dushin, Russell G.,Danishefsky, Samuel J.
, p. 3471 - 3475 (2007/10/02)
The reaction of 3,4,6-tri-O-benzyl-D-glucal (2) with 3,3-dimethyldioxirane gives rise to the 2α,3α-oxirane with high stereoselection. Reaction of this compound with various phenols under alkaline conditions affords aryl 2α-hydroxy-β-glycosides (3a-d). Oxi
