title: Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-D-glucopyranosylorthoesters strategy.
abstract: A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et(3)N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type.
authors: College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
authors: Guangfa
authors: G
authors: Wang
authors: Zhichao
authors: Z
authors: Lu
authors: Ning
authors: N
authors: Ding
authors: Wei
authors: W
authors: Zhang
authors: Peng
authors: P
authors: Wang
authors: Yingxia
authors: Y
authors: Li
mesh_terms: D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D004952:Esters; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D008958:Models, Molecular; D009844:Oligosaccharides / Q000138:chemical synthesis; D013237:Stereoisomerism; D013863:Thioglucosides / Q000737:chemistry
chemical_list: D004952:Esters; D005960:Glucosides; D009844:Oligosaccharides; D013863:Thioglucosides