文献类型：期刊文献

英文题名：Recent Advances in the Chemical Synthesis of C-Glycosides

作者：Yang, You[1];Yu, Biao[2]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

年份：2017

卷号：117

期号：19

起止页码：12281

外文期刊名：CHEMICAL REVIEWS

收录：;EI(收录号：20174204278083);WOS:【SCI-EXPANDED(收录号:WOS:000413056900005)】；

基金：Financial support from the National Thousand Young Talents Program (YC0130518,YC0140103), the Ministry of Science and Technology of China (2012ZX09502-002), the National Natural Science Foundation of China (21432012 and 21621002), the Strategic Priority Research Program of the CAS (XDB20020000), the K. C. Wong Education Foundation, and the Shanghai Pujiang Program (15PJ1401500) is gratefully acknowledged.

语种：英文

外文关键词：Glycosylation - Synthesis (chemical) - Cycloaddition - Metal complexes - Transition metals - Transition metal compounds

摘要：Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg-Backlund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted.