文献类型：期刊文献

英文题名：O-Glycosylation methods in the total synthesis of complex natural glycosides

作者：Yang, You[1];Zhang, Xiaheng[2];Yu, Biao[2]

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

年份：2015

卷号：32

期号：9

起止页码：1331

外文期刊名：NATURAL PRODUCT REPORTS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000360115000004)】；

基金：Financial support from the Ministry of Science and Technology of China (2012ZX09502-002), the National Natural Science Foundation of China (21432012), and the Fundamental Research Funds for the Central Universities (WY1514052), is gratefully acknowledged.

语种：英文

摘要：The total syntheses of 33 complex natural O-glycosides, such as the glycosides of macrocyclic lactones/lactams, enediynes, angucyclines, and anthracyclines, are highlighted, with a major focus being placed on the O-glycosylation reactions which connect the saccharides and the aglycones. These successful O-glycosylation reactions employ such donors as glycosyl bromides, fluorides, iodides, trichloroacetimidates, N-phenyl trifluoroacetimidates, thioglycosides, sulfoxides, heteroaryl thioglycosides, 1-hydroxyl sugars, 1-O-acetates, and ortho-alkynylbenzoates. Each synthesis is depicted starting from the O-glycosylation of the aglycone (or its precursor); the glycosylation conditions and outcomes (yields and stereoselectivities) are discussed, and the subsequent transformations toward the final target, including the elongation of the glycan, the elaboration of the aglycone, and the protecting group manipulations are also given in detail.