Mild Deprotection of the Acetal-type Protecting Groups and Direct Transformation to Another One

DOI

Bibliographic Information

Other Title
  • 水酸基のアセタール型保護基の脱保護と他の保護基への直接変換

Description

Protection of the hydroxy group is essential for the total synthesis of the natural products and the mild removal of the protecting group is strongly desirable. We have developed the novel deprotection of the acetal-type protecting groups of hydroxy group such as THP and MOM ethers by the treatment of silyl triflate-pyridine derivative followed by hydrolysis using H2O as a nucleophile to afford the corresponding alcohols. Here, we report the application of the method to the selective deprotection of other acetal-type (MEM, BOM and SEM) protecting groups in the presence of acid-labile functional groups. Furthermore, we developed the direct transformation of MOM ether to BOM and SEM ethers as well as to the alkyl ethers using the nucleophiles such as alcohols and alkyl (aryl) cuprate reagents.

Journal

Keywords

Details 詳細情報について

  • CRID
    1390282680612161024
  • NII Article ID
    130006997918
  • DOI
    10.14895/hannou.36.0.109.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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