Home >
Community >
Can a benzyl ether be removed in the presence of an ester?
Upvote
25
Downvote
+ Biochemistry
+ Chemoselectivity
Posted by
Nima Oli
Can a benzyl ether be removed in the presence of an ester?
In Wutz's book on protecting groups,[1] I found an example of almost instantaneous reductive debenzylation which leaves an ester untouched:[2]
The use of BCl3 is also possible:[3]
References:
Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 5th ed.; Wiley: Hoboken, NJ, 2014, p 131.
Sulikowski, M. M.; Davies, G. E. R. E.; Smith, A. B., III. Avermectin–milbemycin synthetic studies. Part 7. An approach to the southern hemisphere of milbemycin α1. J. Chem. Soc., Perkin Trans. 11992, 979–989. DOI: 10.1039/P19920000979.
Williams, D. R.; Brown, D. L.; Benbow, J. W. Studies of Stemona alkaloids. Total synthesis of (+)-croomine. J. Am. Chem. Soc.1989,111 (5), 1923–1925. DOI: 10.1021/ja00187a081.
In Wutz's book on protecting groups,[1] I found an example of almost instantaneous reductive debenzylation which leaves an ester untouched:[2]
The use of BCl3 is also possible:[3]
References:
Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 5th ed.; Wiley: Hoboken, NJ, 2014, p 131.
Sulikowski, M. M.; Davies, G. E. R. E.; Smith, A. B., III. Avermectin–milbemycin synthetic studies. Part 7. An approach to the southern hemisphere of milbemycin α1. J. Chem. Soc., Perkin Trans. 11992, 979–989. DOI: 10.1039/P19920000979.
Williams, D. R.; Brown, D. L.; Benbow, J. W. Studies of Stemona alkaloids. Total synthesis of (+)-croomine. J. Am. Chem. Soc.1989,111 (5), 1923–1925. DOI: 10.1021/ja00187a081.
In Wutz's book on protecting groups,[1] I found an example of almost instantaneous reductive debenzylation which leaves an ester untouched:[2]
The use of BCl3 is also possible:[3]
References:
Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 5th ed.; Wiley: Hoboken, NJ, 2014, p 131.
Sulikowski, M. M.; Davies, G. E. R. E.; Smith, A. B., III. Avermectin–milbemycin synthetic studies. Part 7. An approach to the southern hemisphere of milbemycin α1. J. Chem. Soc., Perkin Trans. 1 1992, 979–989. DOI: 10.1039/P19920000979.
Williams, D. R.; Brown, D. L.; Benbow, J. W. Studies of Stemona alkaloids. Total synthesis of (+)-croomine. J. Am. Chem. Soc. 1989, 111 (5), 1923–1925. DOI: 10.1021/ja00187a081.
In Wutz's book on protecting groups,[1] I found an example of almost instantaneous reductive debenzylation which leaves an ester untouched:[2]
The use of BCl3 is also possible:[3]
References:
Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 5th ed.; Wiley: Hoboken, NJ, 2014, p 131.
Sulikowski, M. M.; Davies, G. E. R. E.; Smith, A. B., III. Avermectin–milbemycin synthetic studies. Part 7. An approach to the southern hemisphere of milbemycin α1. J. Chem. Soc., Perkin Trans. 1 1992, 979–989. DOI: 10.1039/P19920000979.
Williams, D. R.; Brown, D. L.; Benbow, J. W. Studies of Stemona alkaloids. Total synthesis of (+)-croomine. J. Am. Chem. Soc. 1989, 111 (5), 1923–1925. DOI: 10.1021/ja00187a081.
More
VOTE