Synthesis of eight-membered iminocyclitols from D-glucose

Jadhav, Vrushali H. ; Bande, Omprakash P. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2010) Synthesis of eight-membered iminocyclitols from D-glucose Tetrahedron, 66 (15). pp. 2830-2834. ISSN 0040-4020

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The Baylis-Hillman reaction of 3-O-benzyl-α-D-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated α-methylene-β-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Baylis-hillman Reaction; Conjugate Addition; Iminosugars; Diastereoselectivity
ID Code:9733
Deposited On:02 Nov 2010 10:49
Last Modified:31 May 2011 11:48

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