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

来源：

TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY | 2008年 / 20卷 / 114期

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

页码：175 / 185

页数：11

共 50 条

[31] PHENYLSELENOGLYCOSIDES AS NOVEL, VERSATILE GLYCOSYL DONORS - SELECTIVE ACTIVATION OVER THIOGLYCOSIDES
MEHTA, S
PINTO, BM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 35 - CARB
[32] Synthesis of D-fructofuranosides using phenyl thioglycosides as glycosyl donors
Xue, J
CHINESE CHEMICAL LETTERS, 1997, 8 (12) : 1029 - 1030
[33] Simple synthesis of glycosylthiols and thioglycosides by rearrangement of O-glycosyl thionocarbamates
Komor, R.
Kasprzycka, A.
Pastuch-Gawolek, G.
Szeja, W.
CARBOHYDRATE RESEARCH, 2014, 396 : 37 - 42
[34] Synthesis of D-Fructofuranosides Using Phenyl Thioglycosides as Glycosyl Donors
Jun XUE (Chemistry Dopartment. Fudan University Shanghai
ChineseChemicalLetters, 1997, (12) : 0 - 0
[35] Novel triple mutant of an extremophilic glycosyl hydrolase enables the rapid synthesis of thioglycosides
Pillet, Lauriane
Lim, David
Almulhim, Nourah
Benitez-Mateos, Ana, I
Paradisi, Francesca
CHEMICAL COMMUNICATIONS, 2022, 58 (86) : 12118 - 12121
[36] 2-Nitro-thioglycosides: α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors
Peng, Peng
Geng, Yiqun
Goettker-Schnetmann, Inigo
Schmidt, Richard R.
ORGANIC LETTERS, 2015, 17 (06) : 1421 - 1424
[37] 6-O-glycosylation of morphine derivatives using thioglycosides as glycosyl donors
Rukhman, I
Yudovich, L
Nisnevich, G
Gutman, AL
SYNTHESIS-STUTTGART, 2000, (09): : 1241 - 1246
[38] PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULFONES
FERNANDEZMAYORALAS, A
MARRA, A
TRUMTEL, M
VEYRIERES, A
SINAY, P
CARBOHYDRATE RESEARCH, 1989, 188 : 81 - 95
[39] Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates
Crich, D
Sun, SX
TETRAHEDRON, 1998, 54 (29) : 8321 - 8348
[40] Mild and efficient hydrolysis of thioglycosides to glycosyl hemiacetals using N-iodosaccharin
Mandal, Pintu Kumar
Misra, Anup Kumar
SYNLETT, 2007, (08) : 1207 - 1210

← 1 2 3 4 5 →