Recent advances in reagent-controlled stereoselective/stereospecific glycosylation

被引:53
|
作者
Yao, Hui [1 ]
Minh Duy Vu [1 ]
Liu, Xue-Wei [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
基金
新加坡国家研究基金会;
关键词
Glycosylation; Reagent-control; Stereoselectivity; Stereospecificity; O-GLYCOSYLATION; SELECTIVE SYNTHESIS; MANNOSYLATION; THIOUREA; DONORS; MANNOPYRANOSIDES; OLIGOSACCHARIDE; DEOXYGLYCOSIDES; GLYCOSIDATION; CONSTRUCTION;
D O I
10.1016/j.carres.2018.10.006
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The formation of O-glycosidic linkage is arguably one of the most important topics in glycoscience due to the prevalence of O-glycosides in nature. Great efforts have been devoted to this field by many carbohydrate chemists to develop stereoselective/stereospecific glycosylation methodologies. Although glycosyl donor- and acceptor-controlled strategies have significantly progressed, the tedious design and pre-synthesis of substrates could not be avoided. On the other hand, reagent-controlled glycosylation can overcome these challenges and produce the desired selectivity by only altering external factors such as concentration, reagents or other reaction conditions. This mini-review discusses selected recent novel methodologies on reagent-mediated stereo-controlled glycosylation in the last decade, classified by the types of glycosyl donors.
引用
收藏
页码:72 / 81
页数:10
相关论文
共 50 条
  • [21] Reagent-controlled SN2-glycosylation for the direct synthesis of β-linked 2-deoxy-sugars
    Issa, John P.
    Bennett, Clay S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [22] A Reagent-Controlled SN2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars
    Issa, John Paul
    Bennett, Clay S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) : 5740 - 5744
  • [23] Substrate- and Reagent-Controlled Electrophilic Asymmetric Fluorinations
    Cao, Lu-Lu
    Gao, Bing-Lei
    Ma, Shu-Tao
    Liu, Zhao-Peng
    CURRENT ORGANIC CHEMISTRY, 2010, 14 (09) : 889 - 916
  • [24] Reagent-controlled diastereoselective aminations with a new chiral nosyloxycarbamate
    Fioravanti, S
    Morreale, A
    Pellacani, L
    Tardella, PA
    TETRAHEDRON LETTERS, 2003, 44 (15) : 3031 - 3034
  • [25] Reagent-Controlled Divergent Synthesis of C-Glycosides
    Han, Pu-Ren
    Liu, Jianchao
    Liao, Jin-Xi
    Tu, Yuan-Hong
    Sun, Jian-Song
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (17): : 11449 - 11464
  • [26] Stereoselective Construction of β-chiral Homoallyl Functionalities by Substrate- and Reagent-Controlled Iterative 1,2-Metallate Rearrangements
    Linne, Elvira
    Kalesse, Markus
    ORGANIC LETTERS, 2023, 25 (46) : 8210 - 8214
  • [27] ORGN 353-Iterative stereospecific reagent-controlled homologation of boronic esters with enantioenriched main-group chiral carbenoids
    Blakemore, Paul R.
    Burge, Matthew S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [28] Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars
    Nogueira, Jason M.
    Bylsma, Marissa
    Bright, Danielle K.
    Bennett, Clay S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (34) : 10088 - 10092
  • [29] On the nature of the chain-extending species in organolithium initiated stereospecific reagent-controlled homologation reactions using α-chloroalkyl aryl sulfoxides
    Hoyt, Amanda L.
    Blakemore, Paul R.
    TETRAHEDRON LETTERS, 2015, 56 (23) : 2980 - 2982
  • [30] Recent Developments in Stereoselective Chemical Glycosylation
    Ling, Jesse
    Bennett, Clay S.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) : 802 - 813