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Synthesis of Fragments of the Capsular Polysaccharide of Haemophilus Influnzae Type B Part II. Preparation and Structural Analysis of Fragments Comprising two and Three Repeating Units

 

作者: P. Hoogerhout,   C.W. Funke,   J.-R. Mellema,   G.N. Wagenaars,   C.A. A. van Boeckel,   D. Evenberg,   J.T. Poolman,   A.W. M. Lefeber,   G.A. Van Der Marel,   J.H. Van Booma,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1988)
卷期: Volume 7, issue 2  

页码: 399-416

 

ISSN:0732-8303

 

年代: 1988

 

DOI:10.1080/07328308808058933

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The synthesis of spacer-containing fragments of the capsular poly-saccharide of H.influenzas, comprising two and three repeating units (9aand9b, respectively), is presented. Ribosylribitol building blocks1and2were coupled with bis [1-benzotriazolyl]-2-chlorophenyl phosphate (3) to give the phosphotriester derivative5a(72%), which was selectively deprotected at O-5 of the terminal ribitol residue (cleavage of the trans-1-propenyl ether) to afford compound6a(82%). Repeated coupling of building block2with6a(chain elongation), followed by propenyl- cleavage, gave analogue6b. Both derivatives6aand6bwere coupled with spacer7(chain termination). The fully protected fragments8a(84%) and8b(49%, starting from6a) were thus obtained. Complete deprotection of8aand8bwas achieved in three steps. After purification and cation-exchange,9aand9bwere obtained in 41 and 68% yields, respectively. The structural integrity of the largest fragment (9b) was confirmed by FAB MS and various NMR spectroscopic techniques.

 

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