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.

引用

页码：5130 / 5134

页数：5

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
BLUMBERG, AA
STAVRINOU, SC
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1960, 64 (10) : 1438 - 1442
[3] NEW SYNTHETIC TRICKS - TRIMETHYLSILYL TRIFLATE MEDIATED CLEAVAGE OF HINDERED SILYL ETHERS
BOU, V
VILARRASA, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (04) : 567 - 568
[4] TETRAFLUOROSILANE IS A MILD AND VERY SELECTIVE REAGENT FOR THE CLEAVAGE OF SILYL-PROTECTED ALCOHOLS
COREY, EJ
YI, KY
[J]. TETRAHEDRON LETTERS, 1992, 33 (17) : 2289 - 2290
[5] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
[6] REMOVAL OF TBDMS PROTECTING GROUPS FROM CARBOHYDRATES USING CATALYTIC TRANSFER HYDROGENATION
CORMIER, JF
[J]. 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
CORRIU, RJP
PERZ, R
REYE, C
[J]. TETRAHEDRON, 1983, 39 (06) : 999 - 1009
[8] HYPERVALENT SPECIES OF SILICON - STRUCTURE AND REACTIVITY
CORRIU, RJP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 400 (1-2) : 81 - 106
[9] A SIMPLE AND CONVENIENT METHOD FOR CLEAVAGE OF SILYL ETHERS
CORT, AD
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (05) : 757 - 760
[10] THE TRIISOPROPYLSILYL GROUP AS A HYDROXYL-PROTECTING FUNCTION
CUNICO, RF
BEDELL, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) : 4797 - 4798

← 1 2 3 4 →