Next Article in Journal
Astaxanthin Treatment Reduced Oxidative Induced Pro-Inflammatory Cytokines Secretion in U937: SHP-1 as a Novel Biological Target
Previous Article in Journal
Mass Spectrometry-Based Metabolomics to Elucidate Functions in Marine Organisms and Ecosystems
Article Menu

Export Article

Open AccessCommunication
Mar. Drugs 2012, 10(4), 881-889; https://doi.org/10.3390/md10040881

First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China
*
Author to whom correspondence should be addressed.
Received: 29 January 2012 / Revised: 16 March 2012 / Accepted: 24 March 2012 / Published: 10 April 2012
Full-Text   |   PDF [642 KB, uploaded 24 February 2015]   |  

Abstract

4-Amino-7-(5′-deoxy-β-d-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from d-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1, 2-O-diacetyl-3-O-benzoyl-d-xylofuranose. Its absolute configuration was confirmed. View Full-Text
Keywords: Vorbrüggen glycosylation; total synthesis; pyrrolo[2,3-d]pyrimidine; marine nucleoside Vorbrüggen glycosylation; total synthesis; pyrrolo[2,3-d]pyrimidine; marine nucleoside
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

Sun, J.; Dou, Y.; Ding, H.; Yang, R.; Sun, Q.; Xiao, Q. First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside. Mar. Drugs 2012, 10, 881-889.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top