Practical method for hydroxyl-group protection using strontium metal and readily available silyl chlorides

Author:

Miyoshi Norikazu12ORCID,Miyoshi Aki1,Miyazaki Yasuaki2,Kubo Shigeki2,Ueno Masaharu12ORCID

Affiliation:

1. Department of Natural Science, Graduate School of Advanced Technology and Science, Tokushima University, 2-1 Minami-jousanjima, Tokushima 770-8506, Japan

2. Department of Chemistry, Faculty of Integrated Arts and Sciences, Tokushima University, 1-1 Minami-jousanjima, Tokushima 770-8502, Japan

Abstract

We have found that the etherification of silyl-protected secondary alcohols proceeds smoothly in the presence of strontium metal using silyl chloride instead of the expensive, yet more reactive, and commonly used silyl triflate.

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Reference47 articles.

1. J.Robertson , Protecting Group Chemistry , Oxford University Press , Oxford Chemistry Primers , vol. 95, 2000

2. P. J.Kociesńky , in protecting groups , 3rd edn, Thieme , Stuttgart , 2005

3. P. G. M.Wuts , in Greene's Protective Groups in Organic Synthesis , 5th edn, Wiley , Hoboken , 2014

4. Chemical Approaches to Define the Structure-Activity Relationship of Heparin-like Glycosaminoglycans

5. Use of Organosilicon Reagents as Protective Groups in Organic Synthesis

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