An efficient and selective method for preparing glycosyl sulfoxides by oxidizing glycosyl sulfides with OXONE or t-BuOOH on SiO2

被引:23
作者
Chen, MY
Patkar, LN
Chen, HT
Lin, CC
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Taipei Nursing Coll, Dept Gen Educ, Taipei 112, Taiwan
关键词
OXONE; t-BuOOH; glycosyl sulfoxide; oxidation; silica gel support;
D O I
10.1016/S0008-6215(03)00164-2
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Silica gel adsorbed with OXONE or t-BuOOH was used as a mild oxidant to selectively oxidize glycosyl sulfides to corresponding sulfoxides in good yields and without sulfones formation. This method was also found compatible with various other functional groups in the glycosides. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1327 / 1332
页数:6
相关论文
共 39 条
[1]  
BALICKI R, 1992, LIEBIGS ANN CHEM, P883
[2]   A ROUTE TO ARTIFICIAL GLYCOCONJUGATES AND OLIGOSACCHARIDES VIA ENZYMATICALLY RESOLVED GLYCALS - DRAMATIC EFFECTS OF THE HANDEDNESS OF THE SUGAR DOMAIN UPON THE PROPERTIES OF AN ANTHRACYCLINE DRUG [J].
BERKOWITZ, DB ;
DANISHEFSKY, SJ ;
SCHULTE, GK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4518-4529
[3]   Toward the development of a general chiral auxiliary .5. High diastereofacial selectivity in cycloadditions with trienol silyl ethers: An application to an enantioselective synthesis of (-)-cassioside [J].
Boeckman, RK ;
Liu, YG .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7984-7985
[4]   SURFACE-MEDIATED REACTIONS .5. OXIDATION OF SULFIDES, SULFOXIDES, AND ALKENES WITH TERT-BUTYL HYDROPEROXIDE [J].
BRETON, GW ;
FIELDS, JD ;
KROPP, PJ .
TETRAHEDRON LETTERS, 1995, 36 (22) :3825-3828
[5]   Stereospecific synthesis of α- and β-C-glycosides from glycosyl sulfoxides:: Scope and limitations [J].
Carpintero, M ;
Nieto, I ;
Fernández-Mayoralas, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1768-1774
[6]  
Clark J.H., 1994, CATALYSIS ORGANIC RE
[7]   Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates [J].
Crich, D ;
Sun, SX .
TETRAHEDRON, 1998, 54 (29) :8321-8348
[8]   Direct synthesis of β-mannosides.: Synthesis of β-D-Xyl-(1→2)-β-D-man-(1→4)-α-D-Glc-OMe:: a trisaccharide component of the Hyriopsis schlegelii glycosphingolipid.: Formation of an orthoester from a xylopyranosyl sulfoxide [J].
Crich, D ;
Dai, ZM .
TETRAHEDRON, 1999, 55 (06) :1569-1580
[9]   Direct synthesis of beta-mannopyranosides by the sulfoxide method [J].
Crich, D ;
Sun, SX .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1198-1199
[10]  
DURST T, 1979, COMPREHENSIVE ORGANI, V3, P121