Electrochemical Conversion of Thioglycosides to Glycosyl Triflates

被引:8
|
作者
Nokami, Toshiki [1 ]
Shibuya, Akito [1 ]
Yoshida, Jun-ichi [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan
基金
日本学术振兴会;
关键词
glycosyl triflate; electrochemical glycosylation; thioglycoside;
D O I
10.4052/tigg.20.175
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
Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by low-temperature electrochemical oxidation of thioglycosides, such as thioglucosides, thiogalacto-sides, and thiomannosides, in the presence of tetrabutylammonium triflate (Bu4NOTf) as a supporting electrolyte. The solutions of glycosyl triflates thus obtained were then characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also studied.
引用
收藏
页码:175 / 185
页数:11
相关论文
共 50 条
  • [1] CARB 88-Efficient conversion of thioglycosides into glycosyl sulphones
    Morais, Goreti Ribeiro, V
    Humphrey, Andrew J.
    Falconer, Robert A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [2] A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters
    Ibatullin, FM
    Selivanov, SI
    Shavva, AG
    SYNTHESIS-STUTTGART, 2001, (03): : 419 - 422
  • [3] EFFICIENT CONVERSION OF THIOGLYCOSIDES INTO GLYCOSYL FLUORIDES USING DIMETHYL(METHYLTHIO)SULFONIUM TETRAFLUOROBORATE
    BLOMBERG, L
    NORBERG, T
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (06) : 751 - 760
  • [4] A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters (pg 419, 2001)
    Ibatullin, FM
    Selivanov, SI
    Shavva, AG
    SYNTHESIS-STUTTGART, 2001, (07): : 1110 - 1110
  • [5] Glycosyl Sulfonates Beyond Triflates
    Bennett, Clay S.
    CHEMICAL RECORD, 2021, 21 (11): : 3102 - 3111
  • [6] Evaluation of thioglycosides of Kdo as glycosyl donors
    Mannerstedt, Karin
    Ekelof, Kerstin
    Oscarson, Stefan
    CARBOHYDRATE RESEARCH, 2007, 342 (3-4) : 631 - 637
  • [7] S-(4-Methoxyphenyl) benzenethiosulfinate (MPBT) trifluoromethanesulfonic anhydride:: A convenient system for the generation of glycosyl triflates from thioglycosides
    Crich, D
    Smith, M
    ORGANIC LETTERS, 2000, 2 (25) : 4067 - 4069
  • [8] PHOTOINDUCED GENERATION OF GLYCOSYL CATIONS FROM THIOGLYCOSIDES
    GRIFFIN, GW
    BANDARA, NC
    CLARKE, MA
    TSANG, WS
    GAREGG, PJ
    OSCARSON, S
    SILWANIS, BA
    HETEROCYCLES, 1990, 30 (02) : 939 - 947
  • [9] 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: A potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages
    Crich, D
    Smith, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) : 9015 - 9020
  • [10] Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
    Nokami, Toshiki
    Shibuya, Akito
    Saigusa, Yoshihiro
    Manabe, Shino
    Ito, Yukishige
    Yoshida, Jun-ichi
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 456 - 460