First O-Glycosylation of hydroxamic acids

被引:36
作者
Thomas, Mickael
Gesson, Jean-Pierre
Papot, Sebastien
机构
[1] Univ Poitiers, UMR 6514, F-86022 Poitiers, France
[2] CNRS, F-86022 Poitiers, France
关键词
D O I
10.1021/jo0701839
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 angstrom molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.
引用
收藏
页码:4262 / 4264
页数:3
相关论文
共 22 条
[1]   THE SYNTHESIS OF ARYL-D-GLUCOPYRANOSIDURONIC ACIDS [J].
BOLLENBACK, GN ;
LONG, JW ;
BENJAMIN, DG ;
LINDQUIST, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (12) :3310-3315
[2]   Efficient sialylation with phenyltrifluoroacetimidates as leaving groups [J].
Cai, ST ;
Yu, B .
ORGANIC LETTERS, 2003, 5 (21) :3827-3830
[3]   Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis [J].
Cook, BN ;
Bhakta, S ;
Biegel, T ;
Bowman, KG ;
Armstrong, JI ;
Hemmerich, S ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (36) :8612-8622
[4]  
DU L, 2005, 229 NAT M AM CHEM SO
[5]   Trichostatin D, a new inducer of phenotypic reversion in transformed cells [J].
Hayakawa, Y ;
Nakai, M ;
Furihata, K ;
Shin-Ya, K ;
Seto, H .
JOURNAL OF ANTIBIOTICS, 2000, 53 (02) :179-183
[6]   Tolerability and pharmacokinetics of the collagenase-selective inhibitor Trocade™ in patients with rheumatoid arthritis [J].
Hemmings, FJ ;
Farhan, M ;
Rowland, J ;
Banken, L ;
Jain, R .
RHEUMATOLOGY, 2001, 40 (05) :537-543
[7]   The first total synthesis of trichostatin D [J].
Hosokawa, S ;
Ogura, T ;
Togashi, H ;
Tatsuta, K .
TETRAHEDRON LETTERS, 2005, 46 (02) :333-337
[8]   Potential role of histone deacetylase inhibitors in mesothelioma: Clinical experience with suberoylanilide hydroxamic acid [J].
Krug, Lee M. ;
Curley, Tracy ;
Schwartz, Lawrence ;
Richardson, Stacie ;
Marks, Paul ;
Chiao, Judy ;
Kelly, W. Kevin .
CLINICAL LUNG CANCER, 2006, 7 (04) :257-261
[9]   The synthesis of the glucuronide adduct of Trocade™ [J].
Mitchell, MB ;
Whitcombe, IWA .
TETRAHEDRON LETTERS, 2000, 41 (45) :8829-8834
[10]   Histone deacetylase inhibitors [J].
Monneret, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (01) :1-13