A New Deprotection Procedure of MTM Ether

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

doi:10.1055/s-0034-1379027

A New Deprotection Procedure of MTM Ether

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

PHA - Molecular Pharmaceutical Science

Nagoya University

Research output: Contribution to journal › Article › peer-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 language	English
Article number	st-2014-u0580-l
Pages (from-to)	2498-2502
Number of pages	5
Journal	Synlett
Volume	25
Issue number	17
DOIs	https://doi.org/10.1055/s-0034-1379027
Publication status	Published - 2014 Oct 22

Keywords

deprotection
MTM
protective group
Pummerer rearrangement

Access to Document

10.1055/s-0034-1379027

Cite this

@article{2905cafdb402436fa886391f9cb6a083,

title = "A New Deprotection Procedure of MTM Ether",

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.",

keywords = "deprotection, MTM, protective group, Pummerer rearrangement",

author = "Masaatsu Adachi and Honoka Hashimoto and Ryo Sakakibara and Takuya Imazu and Toshio Nishikawa",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York.",

year = "2014",

month = oct,

day = "22",

doi = "10.1055/s-0034-1379027",

language = "English",

volume = "25",

pages = "2498--2502",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "17",

}

TY - JOUR

T1 - A New Deprotection Procedure of MTM Ether

AU - Adachi, Masaatsu

AU - Hashimoto, Honoka

AU - Sakakibara, Ryo

AU - Imazu, Takuya

AU - Nishikawa, Toshio

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2014/10/22

Y1 - 2014/10/22

N2 - 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.

AB - 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.

KW - deprotection

KW - MTM

KW - protective group

KW - Pummerer rearrangement

UR - http://www.scopus.com/inward/record.url?scp=84937142139&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84937142139&partnerID=8YFLogxK

U2 - 10.1055/s-0034-1379027

DO - 10.1055/s-0034-1379027

M3 - Article

AN - SCOPUS:84937142139

SN - 0936-5214

VL - 25

SP - 2498

EP - 2502

JO - Synlett

JF - Synlett

IS - 17

M1 - st-2014-u0580-l

ER -

A New Deprotection Procedure of MTM Ether

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this