SYNTHESIS OF DIAMINO ACIDS - POTENTIAL LIPOPOLYSACCHARIDE ANTAGONISTS

被引:4
作者
BULUSU, MARC
WALDSTATTEN, P
机构
[1] Sandoz Forschungsinstitut, A-1235 Vienna
关键词
SEPTIC SHOCK; LIPOPOLYSACCHARIDES; ANTAGONISTS; DIAMINO GLUCOSE; DIAMINO ACIDS;
D O I
10.1016/S0040-4039(00)74161-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,4,6-Tri-O-acetyl-2,3-bis(tert-butyloxycarbonamido)-2,3-dideoxy-alpha-D-glucopyranose (8) was prepared through catalytic reduction and in situ tert-butyloxycorbonylation of 1,4,6-tri-O-acetyl-2-azido-2,3-dideoxy-3-nitro-alpha-D-glucopyra?? nose (5). Starting from 8, 4S,5S-bis(3R-hydroxytetradecanamido)octan-1,8-dioic acid (4) was synthesised in a series of steps.
引用
收藏
页码:1859 / 1862
页数:4
相关论文
共 15 条
[1]   A NEW SYNTHESIS OF 2,3-DIAMINO-2,3-DIDEOXY-D-GLUCOSE [J].
BAER, HH ;
NEILSON, T .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04) :1068-&
[2]   FRAGMENTATION AND WITTIG OLEFINATION OF GLUCOSAMINE DERIVATIVES - A SIMPLE ROUTE TO OPEN-CHAIN AMINO-SUGARS AND CHIRAL GLYCEROLS [J].
GIANNIS, A ;
MUNSTER, P ;
SANDHOFF, K ;
STEGLICH, W .
TETRAHEDRON, 1988, 44 (23) :7177-7180
[3]  
GIANNIS A, 1991, LIEBIGS ANN CHEM, P789
[4]  
Haslberger A., 1987, Triangle, V26, P33
[5]   DIPHOSPHORYL LIPID-A DERIVED FROM LIPOPOLYSACCHARIDE (LPS) OF RHODOPSEUDOMONAS-SPHAEROIDES INHIBITS ACTIVATION OF 70Z/3 CELLS BY LPS [J].
KIRKLAND, TN ;
QURESHI, N ;
TAKAYAMA, K .
INFECTION AND IMMUNITY, 1991, 59 (01) :131-136
[6]   LIPID-IVA INHIBITS SYNTHESIS AND RELEASE OF TUMOR-NECROSIS-FACTOR INDUCED BY LIPOPOLYSACCHARIDE IN HUMAN WHOLE-BLOOD EXVIVO [J].
KOVACH, NL ;
YEE, E ;
MUNFORD, RS ;
RAETZ, CRH ;
HARLAN, JM .
JOURNAL OF EXPERIMENTAL MEDICINE, 1990, 172 (01) :77-84
[7]  
MACHER I, 1985, Patent No. 3415102
[8]   DIPHOSPHORYL-LIPID-A OBTAINED FROM THE NONTOXIC LIPOPOLYSACCHARIDE OF RHODOPSEUDOMONAS-SPHAEROIDES IS AN ENDOTOXIN ANTAGONIST IN MICE [J].
QURESHI, N ;
TAKAYAMA, K ;
KURTZ, R .
INFECTION AND IMMUNITY, 1991, 59 (01) :441-444
[9]  
Reckendorf WM, 1969, CHEM BER, V102, P4207
[10]  
RECKENDORF WMZ, 1964, CHEM BER, V97, P1275