A convenient method for regeneration of free thiol from a tert-butyl thioether

Elijah J. Kragulj; Jeffery L. Gustafson; Douglas B. Grotjahn

doi:10.1055/s-2007-991091

A convenient method for regeneration of free thiol from a tert-butyl thioether

Elijah J. Kragulj
, Jeffery L. Gustafson
, Douglas B. Grotjahn

Chemistry

San Diego State University

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed.

Original language	English
Pages (from-to)	2851-2854
Number of pages	4
Journal	Synlett
Issue number	18
DOIs	https://doi.org/10.1055/s-2007-991091
State	Published - Nov 9 2007

Keywords

Deprotection
Tert-butyl
Thioether
Thiol
Trimethyl phosphine

Access to Document

10.1055/s-2007-991091

Cite this

@article{6a33a7de6733494fbc78cea174118c75,

title = "A convenient method for regeneration of free thiol from a tert-butyl thioether",

abstract = "When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed.",

keywords = "Deprotection, Tert-butyl, Thioether, Thiol, Trimethyl phosphine",

author = "Kragulj, \{Elijah J.\} and Gustafson, \{Jeffery L.\} and Grotjahn, \{Douglas B.\}",

year = "2007",

month = nov,

day = "9",

doi = "10.1055/s-2007-991091",

language = "English",

pages = "2851--2854",

journal = "Synlett",

issn = "0936-5214",

number = "18",

}

TY - JOUR

T1 - A convenient method for regeneration of free thiol from a tert-butyl thioether

AU - Kragulj, Elijah J.

AU - Gustafson, Jeffery L.

AU - Grotjahn, Douglas B.

PY - 2007/11/9

Y1 - 2007/11/9

N2 - When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed.

AB - When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed.

KW - Deprotection

KW - Tert-butyl

KW - Thioether

KW - Thiol

KW - Trimethyl phosphine

UR - https://www.scopus.com/pages/publications/36549058173

U2 - 10.1055/s-2007-991091

DO - 10.1055/s-2007-991091

M3 - Article

AN - SCOPUS:36549058173

SN - 0936-5214

SP - 2851

EP - 2854

JO - Synlett

JF - Synlett

IS - 18

ER -

A convenient method for regeneration of free thiol from a tert-butyl thioether

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this