Synthesis of oligomers of tetrahydrofuran amino acids: furanose carbopeptoids

被引:65
作者
Smith, MD
Long, DD
Marquess, DG
Claridge, TDW
Fleet, GWJ
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Glaxo Wellcome Ltd, Stevenage SG1 2NY, Herts, England
[3] Adv Med Inc, S San Francisco, CA 94080 USA
关键词
D O I
10.1039/a805364b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An acid catalysed ring rearrangement of a triflate derivative of D-mannono-gamma-lactone 6 is the key step in the synthesis of the C-glycosyl sugar amino acid derivatives 3 and 4, examples of carbohydrate amino acid building blocks with specific conformational preferences suitable for incorporation into combinatorial amide libraries; homo-oligomerisation via solution phase coupling procedures affords furanose carbopeptoids 1 which adopt novel solution state secondary structures.
引用
收藏
页码:2039 / 2040
页数:2
相关论文
共 18 条
[1]   ACETONIDES OF HEPTONOLACTONES - POWERFUL CHIRONS [J].
BEACHAM, AR ;
BRUCE, I ;
CHOI, S ;
DOHERTY, O ;
FAIRBANKS, AJ ;
FLEET, GWJ ;
SKEAD, BM ;
PEACH, JM ;
SAUNDERS, J ;
WATKIN, DJ .
TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :883-900
[2]   Complex tetrahydrofurans from carbohydrate lactones: Easy access to epimeric C-glycosides of glucofuranose from D-glycero-D-gulo-heptono-1,4-lactone [J].
Bichard, CJF ;
Brandstetter, TW ;
Estevez, JC ;
Fleet, GWJ ;
Hughes, DJ ;
Wheatley, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (17) :2151-2156
[3]   THE RING CONTRACTION OF DELTA-LACTONES WITH LEAVING GROUP ALPHA-SUBSTITUENTS - A STRATEGY FOR THE SYNTHESIS OF 2,5-DISUBSTITUTED HIGHLY FUNCTIONALIZED HOMOCHIRAL TETRAHYDROFURANS [J].
CHOI, SMS ;
MYERSCOUGH, PM ;
FAIRBANKS, AJ ;
SKEAD, BM ;
BICHARD, CJF ;
MANTELL, SJ ;
SON, JC ;
FLEET, GWJ ;
SAUNDERS, J ;
BROWN, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (21) :1605-1607
[4]   Solid phase synthesis of C-terminal carbohydrate modified enkephalins [J].
Drouillat, B ;
Kellam, B ;
Dekany, G ;
Starr, MS ;
Toth, I .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (17) :2247-2250
[5]   TETRAHYDROPYRAN DERIVATIVES FROM GAMMA-HEXONOLACTONES AND DELTA-HEXONOLACTONES [J].
ESTEVEZ, JC ;
FAIRBANKS, AJ ;
HSIA, KY ;
WARD, P ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1994, 35 (20) :3361-3364
[6]   Solution phase synthesis of (1->5)-amide linked sugar amino acid dimers derived from sialic acids [J].
Gervay, J ;
Flaherty, TM ;
Nguyen, C .
TETRAHEDRON LETTERS, 1997, 38 (09) :1493-1496
[7]  
Horton D., 1966, CARBOHYD RES, V2, P251
[8]  
KALWINSH I, 1995, HETEROCYCLES, V40, P939
[9]   Glycosamino acids: New building blocks for combinatorial synthesis [J].
McDevitt, JP ;
Lansbury, PT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (16) :3818-3828
[10]   OXIDATION OF CARBOHYDRATE DERIVATIVES WITH SILVER CARBONATE ON CELITE .5. OXIDATION OF SOME O-ISOPROPYLIDENE ALDOSES WITH UNSUBSTITUTED ANOMERIC HYDROXYL GROUP [J].
MORGENLIE, S .
ACTA CHEMICA SCANDINAVICA, 1972, 26 (06) :2518-+