IMPROVED PROTOCOLS FOR THE SELECTIVE DEPROTECTION OF TRIALKYLSILYL ETHERS USING FLUOROSILICIC ACID

被引：66

作者：

PILCHER, AS ^{[1
]}

DESHONG, P ^{[1
]}

机构：

[1] UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 19期

关键词：

D O I：

10.1021/jo00071a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Improvements for the application of aqueous fluorosilicic acid to the selective cleavage of tert-butyldimethylsilyl ethers in the presence of triisopropylsilyl ethers are described. Deprotection conditions have been optimized for cleavage selectivity, tolerance by acid-labile compounds, and cleavage rate. Mechanistic features of the desilylation reaction are discussed.

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页码：5130 / 5134

页数：5

相关论文

共 32 条

[1]

BATTEN RJ, 1980, SYNTHESIS-STUTTGART, P234

[2] TABULATED FUNCTIONS FOR HETEROGENEOUS REACTION RATES - THE ATTACK OF VITREOUS SILICA BY HYDROFLUORIC ACID [J].

BLUMBERG, AA ;

STAVRINOU, SC .

JOURNAL OF PHYSICAL CHEMISTRY, 1960, 64 (10) :1438-1442

[3] NEW SYNTHETIC TRICKS - TRIMETHYLSILYL TRIFLATE MEDIATED CLEAVAGE OF HINDERED SILYL ETHERS [J].

BOU, V ;

VILARRASA, J .

TETRAHEDRON LETTERS, 1990, 31 (04) :567-568

[4] TETRAFLUOROSILANE IS A MILD AND VERY SELECTIVE REAGENT FOR THE CLEAVAGE OF SILYL-PROTECTED ALCOHOLS [J].

COREY, EJ ;

YI, KY .

TETRAHEDRON LETTERS, 1992, 33 (17) :2289-2290

[5] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[6] REMOVAL OF TBDMS PROTECTING GROUPS FROM CARBOHYDRATES USING CATALYTIC TRANSFER HYDROGENATION [J].

CORMIER, JF .

TETRAHEDRON LETTERS, 1991, 32 (02) :187-188

[7] ACTIVATION OF SILICON HYDROGEN, SILICON OXYGEN, SILICON NITROGEN BONDS IN HETEROGENEOUS PHASE - SOME NEW METHODS IN ORGANIC-SYNTHESIS [J].

CORRIU, RJP ;

PERZ, R ;

REYE, C .

TETRAHEDRON, 1983, 39 (06) :999-1009

[8] HYPERVALENT SPECIES OF SILICON - STRUCTURE AND REACTIVITY [J].

CORRIU, RJP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 400 (1-2) :81-106

[9] A SIMPLE AND CONVENIENT METHOD FOR CLEAVAGE OF SILYL ETHERS [J].

CORT, AD .

SYNTHETIC COMMUNICATIONS, 1990, 20 (05) :757-760

[10] THE TRIISOPROPYLSILYL GROUP AS A HYDROXYL-PROTECTING FUNCTION [J].

CUNICO, RF ;

BEDELL, L .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4797-4798

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