Neopentyl ester protecting groups for arylsulfonic acids

被引:46
作者
Roberts, JC [1 ]
Gao, H [1 ]
Gopalsamy, A [1 ]
Kongsjahju, A [1 ]
Patch, RJ [1 ]
机构
[1] PROCEPT INC,DEPT RAT DRUG DESIGN,CAMBRIDGE,MA 02139
关键词
D O I
10.1016/S0040-4039(96)02302-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report that neopentylsulfonate esters are stable to a variety of standard organic reaction conditions and are easily cleaved to sulfonic acids. We also discuss the use of N-Boc4-amino-2,2-dimethylbutyl-1-sulfonate esters which may be cleaved under conditions that are suitable far solid phase synthesis. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:355 / 358
页数:4
相关论文
共 9 条
[1]   METHYLENE BRIDGE POSITION IN 2-NAPHTHALENSULFONIC ACID FORMALDEHYDE CONDENSATION PRODUCTS - A NMR INVESTIGATION [J].
ARDUINI, A ;
BRILLI, A ;
PAVAN, F ;
POCHINI, A ;
UNGARO, R ;
CORNO, C .
TETRAHEDRON, 1990, 46 (10) :3607-3612
[2]   NITROBENZENESULFONYL PEROXIDES AS REAGENTS FOR AROMATIC SUBSTITUTION [J].
DANNLEY, RL ;
CORBETT, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :153-&
[3]  
KLAMANN D, 1953, BER DTSCH CHEM GES, V86, P1246
[4]   REGIOSPECIFICITY OF REACTIONS OF EPOXIDES AND OXETANES WITH TRIMETHYLSILYL CYANIDE [J].
MULLIS, JC ;
WEBER, WP .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :2873-2875
[5]   SYNTHESIS OF CARBOHYDRATE SULFONATES AND SULFONATE ESTERS [J].
MUSICKI, B ;
WIDLANSKI, TS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4231-4233
[6]   SYNTHESIS OF NUCLEOSIDE SULFONATES AND SULFONES [J].
MUSICKI, B ;
WIDLANSKI, TS .
TETRAHEDRON LETTERS, 1991, 32 (10) :1267-1270
[7]  
PATCH RJ, 1996, IN PRESS BIOORG MED
[8]   RENIN INHIBITORS - DIPEPTIDE ANALOGS OF ANGIOTENSINOGEN UTILIZING A STRUCTURALLY MODIFIED PHENYLALANINE RESIDUE TO IMPART PROTEOLYTIC STABILITY [J].
PLATTNER, JJ ;
MARCOTTE, PA ;
KLEINERT, HD ;
STEIN, HH ;
GREER, J ;
BOLIS, G ;
FUNG, AKL ;
BOPP, BA ;
LULY, JR ;
SHAM, HL ;
KEMPF, DJ ;
ROSENBERG, SH ;
DELLARIA, JF ;
DE, B ;
MERITS, I ;
PERUN, TJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2277-2288
[9]   NITROGEN ANALOGS OF CROWN ETHERS [J].
RICHMAN, JE ;
ATKINS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2268-2270