Molecular Iodine in Protection
and Deprotection Chemistry

Subrato Das; Ruli Borah; Rashmi Rekha Devi; Ashim Jyoti Thakur

doi:10.1055/s-0028-1083503

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Synlett 2008(18): 2741-2762
DOI: 10.1055/s-0028-1083503

ACCOUNT

Molecular Iodine in Protection and Deprotection Chemistry

Subrato Das^a, Ruli Borah^a, Rashmi Rekha Devi^b, Ashim Jyoti Thakur*^a
^a Department of Chemical Sciences, Central University Tezpur, Napaam, Tezpur 784028, Assam, India
Fax: +91(3712)267005/267006; e-Mail: ashim@tezu.ernet.in;
^b Defense Materials and Stores Research and Development Establishment (DMSRDE), Kanpur 208013, Uttar Pradesh, India

Further Information

Publication History

Received 3 April 2008
Publication Date:
01 October 2008 (online)

Abstract
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Abstract

The various reactions involving the protection and deprotection of functional groups effected by molecular iodine are described here.

1 Introduction

2 Iodine in Organic Synthesis

3 Molecular Iodine in Protection and Deprotection Chemistry

3.1 Protection Chemistry

3.1.1 Protection of Hydroxy Groups

3.1.2 Protection of Amines

3.1.3 Protection of Carbonyl Groups

3.2 Deprotection Chemistry

3.2.1 Deprotection of Carboxylic Esters

3.2.2 Hydrolysis of tert-Butyl Esters

3.2.3 Cleavage of p-Methoxybenzyl Ethers

3.2.4 Deprotection of Alkyl and Aryl Silyl Ethers

3.2.5 Cleavage of Allyl Ethers

3.2.6 Cleavage of Prenyl Ethers

3.2.7 Cleavage of Prenyl Carbamates

3.2.8 Selective Removal of Methoxy Protecting Groups in Carbohydrates

3.2.9 Selective Deprotection of Aromatic Acetates

3.2.10 Selective Deprotection of Acetylated Nucleosides

3.2.11 Depyranylation of Alcohols and Phenols

3.2.12 Chemoselective Deprotection of Acetals and Ketals

3.2.13 Chemoselective Hydrolysis of Terminal Acetonides

3.2.14 Deprotection of Thioacetals and Thioketals

3.2.15 Removal of the Amino-Protecting p-Methoxyphenyl Group

4 Conclusion

Key words

iodine - protection - deprotection - chemoselectivity - catalysis

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