Synthesis and Protection of Aryl Sulfates Using the 2,2,2-Trichloroethyl Moiety
- 17 December 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (2) , 209-212
- https://doi.org/10.1021/ol036157o
Abstract
The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield. This approach to aryl sulfate synthesis was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies.Keywords
This publication has 9 references indexed in Scilit:
- Facile Solid-Phase Synthesis of Sulfated Tyrosine-Containing Peptides: Total Synthesis of Human Big Gastrin-II and Cholecystokinin (CCK)-391,2The Journal of Organic Chemistry, 2000
- Synthesis of phosphotyrosine‐containing peptides using bis‐(2, 2, 2‐trichloro)ethyl groups for phosphate protectionChemical Biology & Drug Design, 1997
- Mechanism of Palladium-Catalyzed Transfer Hydrogenolysis of Aryl Chlorides by Formate SaltsThe Journal of Organic Chemistry, 1995
- A new approach to phosphoserine, phosphothreonine and phosphotyrosine synthons and to thiophospho analogsInternational Journal of Peptide and Protein Research, 1995
- Suicide Inactivation of Human Prostatic Acid Phosphatase and a Phosphotyrosine PhosphataseBiochemical and Biophysical Research Communications, 1994
- Mechanism-Based Inactivation of Prostatic Acid PhosphataseScience, 1993
- Further studies on the use of 2,2,2‐trichloroethyl groups for phosphate protection in phosphoserine peptide synthesisInternational Journal of Peptide and Protein Research, 1992
- A method for the sulfation of sugars, employing a stable, aryl sulfate intermediateCarbohydrate Research, 1981
- The Mechanism of the Acid Hydrolysis of Bunte Salts (S-Alkyl and S-Aryl Thiosulfates)1Journal of the American Chemical Society, 1966