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Molecules 2013, 18(4), 3906-3916; doi:10.3390/molecules18043906
Article

Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

1,2,* , 2 and 2
1 School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China 2 Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, HCI, Zürich CH-8093, Switzerland
* Author to whom correspondence should be addressed.
Received: 25 February 2013 / Revised: 21 March 2013 / Accepted: 21 March 2013 / Published: 2 April 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues mimicking the three constitutional elements of mannose, ribose, and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article, a novel guanofosfocin analogue 6, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from known diol 13, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate 8 by alkoxide generated from 7 and a reductive cyclization of 4-N-acyl-2,4-diamino-5-nitrosopyrimidine 19 to form compound 6.
Keywords: guanofosfocin; 8-alkylated guanine; ether-linked pseudodisaccharide; analogues; α-C-glycoside; nitrosopyrimidine guanofosfocin; 8-alkylated guanine; ether-linked pseudodisaccharide; analogues; α-C-glycoside; nitrosopyrimidine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Huang, M.-H.; Duchek, J.; Vasella, A. Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine. Molecules 2013, 18, 3906-3916.

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