American Chemical Society (ACS)
Organic Letters
,  volume 20 ,  issue 24 ,  pages 8043-8046

Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group

Publication type: Journal Article
Publication date: 2018-12-04
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Nonreducing, pH-neutral conditions for the selective cleavage of the 2,2,2-trichloroethoxycarbonyl (Troc) protecting group are reported. Using trimethyltin hydroxide in 1,2-dichloroethane, Troc-protected alcohols, thiols, and amines can be selectively unmasked in the presence of various functionalities that are incompatible with the reducing conditions traditionally used to remove the Troc group. This mild deprotection protocol tolerates a variety of other hydrolytically sensitive and acid/base-sensitive moieties as well.
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GOST |
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GOST Copy
Trost B. M. et al. Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group // Organic Letters. 2018. Vol. 20. No. 24. pp. 8043-8046.
GOST all authors (up to 50) Copy
Trost B. M., Kalnmals C. A., Tracy J. S., Bai W. J. Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group // Organic Letters. 2018. Vol. 20. No. 24. pp. 8043-8046.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b03642
UR - https://doi.org/10.1021/acs.orglett.8b03642
TI - Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group
T2 - Organic Letters
AU - Trost, Barry M.
AU - Kalnmals, Christopher A
AU - Tracy, J S
AU - Bai, Wen Ju
PY - 2018
DA - 2018/12/04
PB - American Chemical Society (ACS)
SP - 8043-8046
IS - 24
VL - 20
PMID - 30511873
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Trost,
author = {Barry M. Trost and Christopher A Kalnmals and J S Tracy and Wen Ju Bai},
title = {Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.8b03642},
number = {24},
pages = {8043--8046},
doi = {10.1021/acs.orglett.8b03642}
}
MLA
Cite this
MLA Copy
Trost, Barry M., et al. “Highly Chemoselective Deprotection of the 2,2,2-Trichloroethoxycarbonyl (Troc) Protecting Group.” Organic Letters, vol. 20, no. 24, Dec. 2018, pp. 8043-8046. https://doi.org/10.1021/acs.orglett.8b03642.