STEREOSELECTIVE GLYCOSYLATION REACTION STARTING FROM 1-O-TRIMETHYLSILYL SUGARS BY USING DIPHENYLTIN SULFIDE AND A CATALYTIC AMOUNT OF ACTIVE ACIDIC SPECIES

被引：37

作者：

MUKAIYAMA, T

MATSUBARA, K

机构：

来源：

CHEMISTRY LETTERS | 1992年 / 06期

关键词：

D O I：

10.1246/cl.1992.1041

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,2-trans-Ribofuranosides are stereoselectively synthesized from 1-O-trimethylsilyl ribofuranose and trimethylsilyl ethers in the presence of a catalytic amount of Me3SiOTf using Ph2Sn=S as an additive, while 1,2-cis-ribofuranosides and 1,2-cis-glucopyranosides are prepared predominantly in the coexistence of LiClO4 in the above reaction.

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页码：1041 / 1044

页数：4

相关论文

共 8 条

[1]

KLEMER A, 1970, LIEBIGS ANN CHEM, V739, P1851

[2] STEREOSELECTIVE 1,2-CIS GLYCOSYLATION REACTION OF 1-O-ACETYLRIBOSE WITH SILYLATED NUCLEOPHILES BY THE PROMOTION OF A NEW CATALYST SYSTEM [J].

MUKAIYAMA, T ;

SHIMPUKU, T ;

TAKASHIMA, T ;

KOBAYASHI, S .

CHEMISTRY LETTERS, 1989, (01) :145-148

[3] AN EFFICIENT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF 1,2-CIS-RIBOFURANOSIDES AND 1,2-TRANS-RIBOFURANOSIDES FROM 1-HYDROXY RIBOFURANOSE BY THE USE OF DIPHENYLTIN SULFIDE AND TRIFLUOROMETHANESULFONIC ANHYDRIDE [J].

MUKAIYAMA, T ;

MATSUBARA, K ;

SUDA, S .

CHEMISTRY LETTERS, 1991, (06) :981-984

[4] THE EVALUATION OF CATALYSTS GENERATED FROM LEWIS-ACIDS AND SILVER PERCHLORATE IN A HIGHLY STEREOSELECTIVE GLYCOSYLATION OF 1-O-ACETYL-D-GLUCOSE [J].

MUKAIYAMA, T ;

KATSURADA, M ;

TAKASHIMA, T .

CHEMISTRY LETTERS, 1991, (06) :985-988

[5] A HIGHLY STEREOSELECTIVE SYNTHESIS OF ALPHA-GLUCOSIDES FROM 1-O-ACETYL GLUCOSE BY USE OF TIN(IV) CHLORIDE-SILVER PERCHLORATE CATALYST SYSTEM [J].

MUKAIYAMA, T ;

TAKASHIMA, T ;

KATSURADA, M ;

AIZAWA, H .

CHEMISTRY LETTERS, 1991, (04) :533-536

[6] 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

[7] COUPLING REACTIONS OF O-(TRIMETHYLSILYL) GLYCOSIDES AND 6-O-(TERT-BUTYLDIPHENYLSILYL)-PROTECTED GALACTOSIDES IN THE PRESENCE OF TRIMETHYLSILYL TRIFLATE - A NEW METHOD OF FORMING BETA-(1-]6)-OLIGOSACCHARIDIC LINKAGES [J].

NASHED, EM ;

GLAUDEMANS, CPJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6116-6118

[8] SIMPLE AND STEREOSELECTIVE SYNTHESIS OF ALPHA AND BETA PHENYLGLUCOSIDES [J].

TIETZE, LF ;

FISCHER, R ;

GUDER, HJ .

TETRAHEDRON LETTERS, 1982, 23 (45) :4661-4664