Synthesis 2015; 47(08): 1163-1169
DOI: 10.1055/s-0034-1379962
paper
© Georg Thieme Verlag Stuttgart · New York

Modulation of the Electronic Properties of Non-innocent (E,E)-Dibenzylideneacetone for Palladium(0)-Mediated Heck Alkenylation of 5-Iodo-2′-deoxyuridine and Scale-Up Studies

Anant R. Kapdi*
a  Institute of Chemical Technology, Mumbai, Nathalal Road, Matunga, Mumbai-400019, India   Email: ar.kapdi@ictmumbai.edu.in
,
Ajay Ardhapure
a  Institute of Chemical Technology, Mumbai, Nathalal Road, Matunga, Mumbai-400019, India   Email: ar.kapdi@ictmumbai.edu.in
,
Yogesh S. Sanghvi
b  Rasayan Inc., 2802 Crystal Ridge Road, Encinitas, CA 92024-6615, USA
› Author Affiliations
Further Information

Publication History

Received: 24 September 2014

Accepted after revision: 08 December 2014

Publication Date:
10 February 2015 (eFirst)

Dedicated to Professor Richard K. Taylor on his 65th birthday

Abstract

Subtle modulation of the electronic properties of the dibenzylideneacetone (dba) ligand allows the development of an efficient protocol for the Heck alkenylation of 5-iodo-2′-deoxyuridine. This protocol enables the large-scale synthesis of commercially important nucleoside building blocks. The isolation of one key molecule was accomplished under column-free conditions on a 10-gram scale.

Supporting Information

 
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