A New Deprotection Procedure of MTM Ether

Masaatsu Adachi, Honoka Hashimoto, Ryo Sakakibara, Takuya Imazu, Toshio Nishikawa

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A new deprotection procedure of methylthiomethyl (MTM) ether, a protective group for the hydroxy group, was developed. MTM was oxidized with MCPBA or Oxone, and the resulting sulfoxide was treated under conditions of the Pummerer rearrangement, to give acetoxy sulfide and/or acetoxy acetal. Alkaline hydrolysis of the products provided the unprotected alcohols in good yields. Details of the reactions using several different substrates are described.

Original languageEnglish
Article numberst-2014-u0580-l
Pages (from-to)2498-2502
Number of pages5
JournalSynlett
Volume25
Issue number17
DOIs
Publication statusPublished - 2014 Oct 22
Externally publishedYes

Keywords

  • MTM
  • Pummerer rearrangement
  • deprotection
  • protective group

ASJC Scopus subject areas

  • Organic Chemistry

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