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Alternative synthesis and regioselective coupling of 1,6‐anhydro‐2‐azido‐ and ‐2‐phthalimido‐2‐deoxy‐β‐D‐galactopyranose

 

作者: M. Kloosterman,   D. de Wit,   J. H. van Boom,   H. T. de Hey,  

 

期刊: Recueil des Travaux Chimiques des Pays‐Bas  (WILEY Available online 1986)
卷期: Volume 105, issue 7‐8  

页码: 229-231

 

ISSN:0165-0513

 

年代: 1986

 

DOI:10.1002/recl.19861050707

 

出版商: WILEY‐VCH Verlag

 

数据来源: WILEY

 

摘要:

AbstractEasily accessible 1,6‐anhydro‐3,4‐isopropylidene‐β‐D‐galactopyranose has been converted in four steps (i.e., oxidation, reduction, triflation andWaldeninversion with lithium azide or potassium phthalimide) into 1,6‐anhydro‐2‐azido‐ or ‐2‐phthalimido‐2‐deoxy‐3,4‐O‐isopropylidene‐β‐D‐galacto‐ pyranose. The 2‐azido derivative, obtained after acidolysis of the isopropylidene group, could be coupled regioselectively at the hydroxyl group at C‐4 with either 1,3,4,6‐tetra‐O‐acetyl‐2‐phthalimido‐2‐deoxy‐β‐D‐ glucopyranose or 3,4,6‐tri‐O‐acetyl‐2‐phthalimido‐2‐deoxy‐α‐D‐glucopyranosyl bromide in the presence of the soluble cataly

 

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