Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol

被引：24

作者：

Al-Mughaid, H ^{[1
]}

Grindley, TB ^{[1
]}

机构：

[1] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4J3, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 04期

关键词：

D O I：

10.1021/jo052045u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nonavalent glycodendrimer bearing terminal alpha-D-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having three 2-hydroxyethyl ether substituents. Two efficient routes were developed for the synthesis of the pentaerythritol-based core (17), which has three terminal propargyl ethers. Conditions were found under which the triple Sonogashira coupling reaction of the dendron and the tri-O-propargyl ether (17) proceeded efficiently. The product was deprotected and it and precursors were fully characterized by NMR spectroscopy and FT-ICR mass spectrometry.

引用

页码：1390 / 1398

页数：9

共 56 条

[1] Novel disaccharide inhibitors of human glioma cell division [J].

Aguilera, B ;

Romero-Ramirez, L ;

Abad-Rodriguez, J ;

Corrales, G ;

Nieto-Sampedro, M ;

Fernández-Mayoralas, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (23) :4599-4606

[2] Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli [J].

Appeldoorn, CCM ;

Joosten, JAF ;

el Maate, FA ;

Dobrindt, U ;

Hacker, J ;

Liskamp, RMJ ;

Khan, AS ;

Pieters, RJ .

TETRAHEDRON-ASYMMETRY, 2005, 16 (02) :361-372

[3] Cutting edge: Carbohydrate profiling identifies new pathogens that interact with dendritic cell-specific ICAM-3-grabbing nonintegrin on dendritic cells [J].

Appelmelk, BJ ;

van Die, I ;

van Vliet, SJ ;

Vandenbroucke-Grauls, CMJE ;

Geijtenbeek, TBH ;

van Kooyk, Y .

JOURNAL OF IMMUNOLOGY, 2003, 170 (04) :1635-1639

[4] A highly regio- and chemoselective reductive cleavage of benzylidene acetals with EtAlCl2-Et3SiH [J].

Balakumar, V ;

Aravind, A ;

Baskaran, S .

SYNLETT, 2004, (04) :647-650

[5]

Berglund J, 2003, ADV EXP MED BIOL, V535, P33

[6] Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives [J].

Bien, F ;

Ziegler, T .

TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :781-790

[7] STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES [J].

BOCK, K ;

PEDERSEN, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03) :293-299

[8] Receptor binding studies disclose a novel class of high-affinity inhibitors of the Escherichia coli FimH adhesin [J].

Bouckaert, J ;

Berglund, J ;

Schembri, M ;

De Genst, E ;

Cools, L ;

Wuhrer, M ;

Hung, CS ;

Pinkner, J ;

Slättegård, R ;

Zavialov, A ;

Choudhury, D ;

Langermann, S ;

Hultgren, SJ ;

Wyns, L ;

Klemm, P ;

Oscarson, S ;

Knight, SD ;

De Greve, H .

MOLECULAR MICROBIOLOGY, 2005, 55 (02) :441-455

[9]

Burns CJ, 1999, AUST J CHEM, V52, P1071

[10] X-ray structure of the FimC-FimH chaperone-adhesin complex from uropathogenic Escherichia coli [J].

Choudhury, D ;

Thompson, A ;

Stojanoff, V ;

Langermann, S ;

Pinkner, J ;

Hultgren, SJ ;

Knight, SD .

SCIENCE, 1999, 285 (5430) :1061-1066

← 1 2 3 4 5 6 →