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
[11]   Chiral cyclopentane-based mimics of D-myo-inositol 1,4,5-trisphosphate from D-glucose [J].
Jenkins, DJ ;
Riley, AM ;
Potter, BVL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7719-7726
[12]   Use of solid supported nucleophiles and electrophiles for the purification of non-peptide small molecule libraries [J].
Kaldor, SW ;
Siegel, MG ;
Fritz, JE ;
Dressman, BA ;
Hahn, PJ .
TETRAHEDRON LETTERS, 1996, 37 (40) :7193-7196
[13]   SAFETY CATCH PRINCIPLE IN SOLID PHASE PEPTIDE SYNTHESIS [J].
KENNER, GW ;
MCDERMOT.JR ;
SHEPPARD, RC .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (12) :636-&
[14]   Carbohydrate-carbohydrate interactions in water with glycophanes as model systems [J].
Morales, JC ;
Zurita, D ;
Penadés, S .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9212-9222
[15]   SYNTHESIS OF LIGANDS RELATED TO THE O-SPECIFIC ANTIGEN OF SHIGELLA-DYSENTERIAE TYPE-1 .6. SYNTHESIS OF METHYL O-ALPHA-L-RHAMNOPYRANOSYL-(1 -] 2)-ALPHA-D-GALACTOPYRANOSIDES SPECIFICALLY DEOXYGENATED AT POSITION-3, POSITION-4, OR POSITION-6 OF THE GALACTOSE RESIDUE [J].
MULARD, LA ;
KOVAC, P ;
GLAUDEMANS, CPJ .
CARBOHYDRATE RESEARCH, 1994, 251 :213-232
[16]   SPECIFIC REMOVAL OF ORTHO-METHOXYBENZYL PROTECTION BY DDQ OXIDATION [J].
OIKAWA, Y ;
YOSHIOKA, T ;
YONEMITSU, O .
TETRAHEDRON LETTERS, 1982, 23 (08) :885-888
[17]   Synthesis of sulfated trisaccharide ligands for the selectins [J].
Sanders, WJ ;
Manning, DD ;
Koeller, KM ;
Kiessling, LL .
TETRAHEDRON, 1997, 53 (48) :16391-16422
[18]  
Sharma GVM, 1999, J ORG CHEM, V64, P8943
[19]   A NEW, CONVENIENT REDUCTIVE PROCEDURE FOR THE DEPROTECTION OF 4-METHOXYBENZYL (MPM) ETHERS TO ALCOHOLS [J].
SRIKRISHNA, A ;
VISWAJANANI, R ;
SATTIGERI, JA ;
VIJAYKUMAR, D .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5961-5962
[20]   A METHOD FOR TRANSFER OF LABELED METHYL-GROUPS [J].
TOWNSEND, CA ;
THEIS, AB .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1697-1699