A catalytic and stereoselective glycosylation with glucopyranosyl fluoride by using various protic acids

被引：37

作者：

Jona, H ^{[1
]}

Mandai, H ^{[1
]}

Mukaiyama, T ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

CHEMISTRY LETTERS | 2001年 / 05期

关键词：

D O I：

10.1246/cl.2001.426

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic and stereoselective glycosylation with glucosyl fluoride was effectively performed by using a catalytic amount of various protic acids. When the glycosylation was carried out, for example, using perchloric acid (HClO4) in diethyl ether (Et2O), the major products were alpha -glycosides while beta -stereoselectivity was observed when tetrakis(pentafluorophenyl)boric acid [HB(C6F5)(4)] was used in a mixed solvent of trifluoromethylbenzene (BTF)-pivalonitrile ((BuCN)-Bu-t) = (5:1). The stereoselectivity was controlled by not only the effect of solvent but also by the nature of counter anion of the catalyst such as B(C6F5)(4)(-) or ClO4-.

引用

页码：426 / 427

页数：2

共 19 条

[1] 1,2-Cis selective glycosylation with glycosyl fluoride by using a catalytic amount of trifluoromethanesulfonic acid (TfOH) in the coexistence of molecular sieve 5Å (MS5Å) [J].

Jona, H ;

Takeuchi, K ;

Mukaiyama, T .

CHEMISTRY LETTERS, 2000, (11) :1278-1279

[2] Cyclization of polyenes. Part 57. An efficient construction of trinervitane and kempane skeletons from the common intermediate [J].

Kato, T ;

Tanaka, M ;

Hoshikawa, M ;

Yagi, M .

TETRAHEDRON LETTERS, 1998, 39 (41) :7553-7556

[3] KINETICS OF REACTIONS OF TERT-BUTYL CHLORIDE AND [H-2(9)]TERT-BUTYL CHLORIDE WITH SILVER SALTS IN ACETONITRILE [J].

KEVILL, DN ;

SUTTHOFF, RF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (02) :201-206

[4] IODONIUM ION GENERATED INSITU FROM N-IODOSUCCINIMIDE AND TRIFLUOROMETHANESULFONIC ACID PROMOTES DIRECT LINKAGE OF DISARMED PENT-4-ENYL GLYCOSIDES [J].

KONRADSSON, P ;

MOOTOO, DR ;

MCDEVITT, RE ;

FRASEREID, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (03) :270-272

[5] Trifluoromethanesulfonic acid (TfOH)-catalyzed stereoselective glycosylation using glycosyl fluoride [J].

Mukaiyama, T ;

Jona, H ;

Takeuchi, K .

CHEMISTRY LETTERS, 2000, (06) :696-697

[6] Catalytic and stereoselective glycosylation with disarmed glycosyl fluoride by using a combination of stannous(II) chloride (SnCl2) and silver tetrakis(pentafluorophenyl)borate [AgB(C6F5)4] as a catalyst [J].

Mukaiyama, T ;

Maeshima, H ;

Jona, H .

CHEMISTRY LETTERS, 2001, (05) :388-389

[7] AN EFFICIENT METHOD FOR GLUCOSYLATION OF HYDROXY COMPOUNDS USING GLUCOPYRANOSYL FLUORIDE [J].

MUKAIYAMA, T ;

MURAI, Y ;

SHODA, S .

CHEMISTRY LETTERS, 1981, (03) :431-432

[8] A FACILE SYNTHESIS OF ALPHA-GLUCOSIDES AND ALPHA-RIBOSIDES FROM THE CORRESPONDING 1-O-ACYL SUGARS AND ALCOHOLS IN THE PRESENCE OF TRITYL PERCHLORATE [J].

MUKAIYAMA, T ;

KOBAYASHI, S ;

SHODA, S .

CHEMISTRY LETTERS, 1984, (06) :907-910

[9]

Mukaiyama T, 2000, HELV CHIM ACTA, V83, P1901, DOI 10.1002/1522-2675(20000809)83:8<1901::AID-HLCA1901>3.0.CO

[10]

2-Q

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