Combinatorial solid-phase synthesis using D-Galactose as a chiral five-dimension-diversity scaffold

被引:55
作者
Kallus, C
Opatz, T
Wunberg, T
Schmidt, W
Henke, S
Kunz, H [1 ]
机构
[1] Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany
[2] Hoechst Marion Roussel Deutschland GMBH, D-65926 Frankfurt, Germany
关键词
combinatorial chemistry; carbohydrates; protecting groups; solid-phase synthesis;
D O I
10.1016/S0040-4039(99)01690-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
All five hydroxy groups of galactose as the scaffold are used for selective coupling of side chains in a combinatorial methodology by application of a set of orthogonally stable protecting groups in combination with a thioglycoside anchor. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7783 / 7786
页数:4
相关论文
共 21 条
[1]  
[Anonymous], 1998, ANGEW CHEM, V110, P2620
[2]  
[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881
[3]  
BALKENHOHL C, 1996, ANGEW CHEM, V108, P2136
[4]   PEPTIDOSTEROIDAL RECEPTORS FOR OPIOID-PEPTIDES - SEQUENCE-SELECTIVE BINDING USING A SYNTHETIC RECEPTOR LIBRARY [J].
BOYCE, R ;
LI, G ;
NESTLER, HP ;
SUENAGA, T ;
STILL, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7955-7956
[5]   A MILD PROCEDURE FOR THE REGIOSPECIFIC BENZYLATION AND ALLYLATION OF POLYHYDROXY-COMPOUNDS VIA THEIR STANNYLENE DERIVATIVES IN NON-POLAR SOLVENTS [J].
DAVID, S ;
THIEFFRY, A ;
VEYRIERES, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1796-1801
[6]   REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES [J].
DAVID, S ;
HANESSIAN, S .
TETRAHEDRON, 1985, 41 (04) :643-663
[7]   Design, synthesis, and evaluation of the multidrug resistance reversing activity of D-glucose mimetics of hapalosin [J].
Dinh, TQ ;
Smith, CD ;
Du, XH ;
Armstrong, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :981-987
[8]   Glycopeptide synthesis using O-pentafluorophenyluronium salts as novel condensing reagents [J].
Habermann, J ;
Kunz, H .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (03) :233-239
[9]   DE-NOVO DESIGN AND SYNTHESIS OF SOMATOSTATIN NONPEPTIDE PEPTIDOMIMETICS UTILIZING BETA-D-GLUCOSE AS A NOVEL SCAFFOLDING [J].
HIRSCHMANN, R ;
NICOLAOU, KC ;
PIETRANICO, S ;
LEAHY, EM ;
SALVINO, J ;
ARISON, B ;
CICHY, MA ;
SPOORS, PG ;
SHAKESPEARE, WC ;
SPRENGELER, PA ;
HAMLEY, P ;
SMITH, AB ;
REISINE, T ;
RAYNOR, K ;
MAECHLER, L ;
DONALDSON, C ;
VALE, W ;
FREIDINGER, RM ;
CASCIERI, MR ;
STRADER, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12550-12568
[10]   New methodologies for the synthesis of compound libraries [J].
Kobayashi, S .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) :1-15