Glycosyl fluoride
-
- MUKAIYAMA Teruaki
- The Kitasato Institute, Center for Basic Research
-
- JONA Hideki
- The Kitasato Institute, Center for Basic Research Tsukuba Research Institute, Banyu Pharmaceutical Co., Ltd.
Bibliographic Information
- Other Title
-
- Glycosyl fluoride--A superb glycosyl donor in glycosylation
- A superb glycosyl donor in glycosylation
Search this article
Abstract
Catalytic and stereoselective glycosylations using glycosyl fluorides are described: 1) activation of armed glycosyl fluorides by trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] catalyst in trifluoromethylbenzene (BTF)-pivalonitrile ('BuCN)(5:1) to afford the corresponding disaccharides in high yields with good to high β-stereoselectivity; 2) activation of disarmed glycosyl fluorides by the combined use of silver tetrakis(pentafluorophenyl)borate [AgB(C6F5)4] and stannous chloride (SnCl2) or stannic chloride<br>(SnCl4); and 3) selective α or β glycosylation using glycosyl fluoride by an appropriate choice of erotic acid catalysts and solvents. Also, the effect of counter anions of erotic acid catalysts on controlling the stereo-selectivities of glycosylation is newly noted. Finally, efficient one-pot sequential syntheses of trisaccharide, F1α antigen, and branched heptasaccharide are demonstrated.
Journal
-
- Proceedings of the Japan Academy, Series B
-
Proceedings of the Japan Academy, Series B 78 (4), 73-83, 2002
The Japan Academy
- Tweet
Keywords
Details 詳細情報について
-
- CRID
- 1390282679123548416
-
- NII Article ID
- 130000907845
-
- NII Book ID
- AA00785485
-
- ISSN
- 13492896
- 03862208
-
- NDL BIB ID
- 6179022
-
- Text Lang
- en
-
- Data Source
-
- JaLC
- NDL
- Crossref
- CiNii Articles
-
- Abstract License Flag
- Disallowed