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Synthesis 2007(2): 294-298  
DOI: 10.1055/s-2006-958943
PAPER
© Georg Thieme Verlag Stuttgart · New York

Conversion of Glycals to 1-Azido-2-iodo Sugars Using N-Iodosuccinimide/Sodium­ Azide or Potassium Iodide/Oxone Reagent Systems: Application in the Synthesis of Methyl N-Acetyl-α-d-lividosaminide

Girish K. Rawala, Shikha Rania, K. P. Madhusudananb, Yashwant D. Vankar*a
a Chemistry Department, Indian Institute of Technology Kanpur, Kanpur 208016, India
b SAIF, Central Drugs Research Institute, Chhattar Manzil Palace, Lucknow 226001, India
Fax: +91(512)2597436; e-Mail: vankar@iitk.ac.in;
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Publication History

Received 11 September 2006
Publication Date:
14 December 2006 (online)

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Abstract

Glycals are readily converted into the corresponding 2-deoxy-2-iodoglycosyl azides, in good to excellent yields in a short time, upon treatment with N-iodosuccinimide/sodium azide or potassium iodide/Oxone reagent systems. One of these 1-azido-2-iodo sugars was converted into methyl N-acetyl-α-d-lividosaminide.

Key words

glycals - N-iodosuccinimide - sodium azide - potassium iodide - Oxone - 1-azido-2-iodo sugar - methyl N-acetyl-α-d-livido­s­aminide