p-methoxybenzyl ether cleavage by polymer-supported sulfonamides

被引:22
作者
Hinklin, RJ
Kiessling, LL
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
[2] Univ Wisconsin, Dept Biochem, Madison, WI 53706 USA
关键词
D O I
10.1021/ol025514c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] p-Methoxybenzyl ethers have been found to transfer from alcohols to sulfonamides in the presence of catalytic trifluoromethanesulfonic acid. This process for protecting group removal can be performed in solution with yields >94%. Through the use of sulfonamide-functionalized ("safety-catch") resins, p-methoxybenzyl ethers can be cleaved in excellent yields with minimal purification.
引用
收藏
页码:1131 / 1133
页数:3
相关论文
共 24 条
[1]   AMINE PRODRUGS WHICH UTILIZE HYDROXY AMIDE LACTONIZATION .1. A POTENTIAL REDOX-SENSITIVE AMIDE PRODRUG [J].
AMSBERRY, KL ;
BORCHARDT, RT .
PHARMACEUTICAL RESEARCH, 1991, 8 (03) :323-330
[2]   Activation method to prepare a highly reactive acylsulfonamide ''safety-catch'' linker for solid-phase synthesis [J].
Backes, BJ ;
Virgilio, AA ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3055-3056
[3]   Polymer-supported quenching reagents for parallel purification [J].
Booth, RJ ;
Hodges, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4882-4886
[4]   THE PARA-METHOXYBENZYL GROUP AS PROTECTIVE GROUP OF THE ANOMERIC CENTER - SELECTIVE CONVERSIONS OF HYDROXY-GROUPS INTO BROMO GROUPS IN PARA-METHOXYBENZYL 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE [J].
CLASSON, B ;
GAREGG, PJ ;
SAMUELSSON, B .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :419-422
[5]   THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C [J].
DEMEDEIROS, EF ;
HERBERT, JM ;
TAYLOR, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2725-2730
[6]  
Eames J, 2001, EUR J ORG CHEM, V2001, P1213
[7]   Chemical library purification strategies based on principles of complementary molecular reactivity and molecular recognition [J].
Flynn, DL ;
Crich, JZ ;
Devraj, RV ;
Hockerman, SL ;
Parlow, JJ ;
South, MS ;
Woodard, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4874-4881
[8]  
Green T.W., 1999, PROTECTIVE GROUPS OR, V3rd
[9]   Glycosyl sulfonylcarbamates: New glycosyl donors with tunable reactivity [J].
Hinklin, RJ ;
Kiessling, LL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) :3379-3380
[10]   CLEAVAGE OR ACETYL-DE-ALKYLATION OF 4-METHOXYBENZYL (MPM) ETHERS USING ACETIC-ACID [J].
HODGETTS, KJ ;
WALLACE, TW .
SYNTHETIC COMMUNICATIONS, 1994, 24 (08) :1151-1155