Simple silyl linker for the solid phase organic synthesis of aryl-containing molecules

被引：38

作者：

Newlander, KA ^{[1
]}

Chenera, B ^{[1
]}

Veber, DF ^{[1
]}

Yim, NCF ^{[1
]}

Moore, ML ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT MED CHEM,KING OF PRUSSIA,PA 19406

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 20期

关键词：

D O I：

10.1021/jo9620472

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have designed a simple (dimethylsilyl)propionic acid linker for the solid phase synthesis of aryl-containing organic compounds. The linker is cleaved smoothly with trifluoroacetic acid either in solution or in the vapor phase to release the unsubstituted aryl moiety, Using this linker, we have successfully demonstrated the solid phase synthesis of a test compound which involved alkylation, acylation, and Mitsunobu reactions.

引用

页码：6726 / 6732

页数：7

共 12 条

[1] AN IMPROVED PREPARATION OF BENZHYDRYLAMINE RESIN [J].

BRYAN, WM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3371-3372

[2]

CHENERA B, 1995, J AM CHEM SOC, V117, P11999

[3] SYNTHESIS OF SOME (TRIMETHYLSILYL)METHYL COMPOUNDS [J].

CUNICO, RF ;

GILL, HS .

ORGANOMETALLICS, 1982, 1 (01) :1-3

[4] Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction [J].

Han, YX ;

Walker, SD ;

Young, RN .

TETRAHEDRON LETTERS, 1996, 37 (16) :2703-2706

[5] CREATION AND FUNCTIONAL SCREENING OF A MULTIUSE PEPTIDE LIBRARY [J].

JAYAWICKREME, CK ;

GRAMINSKI, GF ;

QUILLAN, JM ;

LERNER, MR .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (05) :1614-1618

[6]

KAISER E, 1970, ANAL BIOCHEM, V34, P594

[7] POLYMER-SUPPORTED MITSUNOBU ETHER FORMATION AND ITS USE IN COMBINATORIAL CHEMISTRY [J].

KRCHNAK, V ;

FLEGELOVA, Z ;

WEICHSEL, AS ;

LEBL, M .

TETRAHEDRON LETTERS, 1995, 36 (35) :6193-6196

[8] DETECTION OF A CATALYTIC ANTIBODY SPECIES ACYLATED AT THE ACTIVE-SITE BY ELECTROSPRAY MASS-SPECTROMETRY [J].

KREBS, JF ;

SIUZDAK, G ;

DYSON, HJ ;

STEWART, JD ;

BENKOVIC, SJ .

BIOCHEMISTRY, 1995, 34 (03) :720-723

[9] A SILICON-BASED LINKER FOR TRACELESS SOLID-PHASE SYNTHESIS [J].

PLUNKETT, MJ ;

ELLMAN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6006-6007

[10] DISCOVERY OF BIOLOGICALLY-ACTIVE PEPTIDES IN RANDOM LIBRARIES - SOLUTION-PHASE TESTING AFTER STAGED ORTHOGONAL RELEASE FROM RESIN BEADS [J].

SALMON, SE ;

LAM, KS ;

LEBL, M ;

KANDOLA, A ;

KHATTRI, PS ;

WADE, S ;

PATEK, M ;

KOCIS, P ;

KRCHNAK, V ;

THORPE, D ;

FELDER, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (24) :11708-11712

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