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Lengthening of tetrose and pentose carbon chains by vinylation reactions

 

作者: D. J. Walton,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1968)
卷期: Volume 46, issue 23  

页码: 3679-3684

 

ISSN:0008-4042

 

年代: 1968

 

DOI:10.1139/v68-608

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

Vinylation of 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose gave a 1.3:1 mixture of 1,2:3,4-di-O-isopropylidene-6-heptene-L-gulo(andD-manno)-1,2,3,4,5-pentol (1aand2a). Successive ozonolysis and hydrolysis of the mixture of1aand2agaveD-glucose andD-mannose in a ratio of 1.4:1. Vinylation of 2,4-O-ethylidene-aldehydo-D-erythrose gave a 3.9:1 mixture of 1,3-O-ethylidene-5-hexene-L-ribo(andD-lyxo)-1,2,3,4-tetrol (3aand4a), which was degraded to formD-ribose andD-arabinose in a ratio of 4:1. The configuration of each of theC-vinyl compounds1a,2a,3a, and4awas assigned by degradation to the corresponding aldose.

 

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