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Volumn 73, Issue 2, 2008, Pages 752-755

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted facile deprotection of N,O-acetonides

Author keywords

[No Author keywords available]

Indexed keywords

ACETONIDES; FACILE DEPROTECTION; PROTECTING GROUPS; REACTION CONDITIONS;

EID: 40949155085     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7021923     Document Type: Article
Times cited : (16)

References (23)
  • 2
    • 29544441466 scopus 로고    scopus 로고
    • For some recent studies on the deprotection of O,O-acetonides, see: (a) Coste, G.; Gerber-Lemaire, S. Tetrahedron Lett. 2006, 47, 671-674.
    • For some recent studies on the deprotection of O,O-acetonides, see: (a) Coste, G.; Gerber-Lemaire, S. Tetrahedron Lett. 2006, 47, 671-674.
  • 7
    • 19544378854 scopus 로고    scopus 로고
    • For some recent reports on the deprotection of N,O-acetonides, see: (a) Cong, X.; Hu, F.; Liu, K.-G.; Liao, Q.-J.; Yao, Z.-J. J. Org. Chem. 2005, 70, 4514-4516.
    • For some recent reports on the deprotection of N,O-acetonides, see: (a) Cong, X.; Hu, F.; Liu, K.-G.; Liao, Q.-J.; Yao, Z.-J. J. Org. Chem. 2005, 70, 4514-4516.
  • 12
    • 0033583303 scopus 로고    scopus 로고
    • We are thankful to one of the reviewers of this manuscript for bringing to our attention the following publication, observing the cleavage of an O,O-acetonide (albeit as a minor reaction), presumably by TMSOTf. Procopiou, P. A.; Lynn, S. M.; Roberts, A. D. Tetrahedron 1999, 55, 3649-3656.
    • We are thankful to one of the reviewers of this manuscript for bringing to our attention the following publication, observing the cleavage of an O,O-acetonide (albeit as a minor reaction), presumably by TMSOTf. Procopiou, P. A.; Lynn, S. M.; Roberts, A. D. Tetrahedron 1999, 55, 3649-3656.
  • 13
    • 41149119455 scopus 로고    scopus 로고
    • We thank one of the reviewers of this manuscript for suggesting an alternative mechanistic pathway (via the formation of II and IV, Scheme 3) leading to the observed acetonide cleavage.
    • We thank one of the reviewers of this manuscript for suggesting an alternative mechanistic pathway (via the formation of II and IV, Scheme 3) leading to the observed acetonide cleavage.
  • 21
    • 41149168656 scopus 로고    scopus 로고
    • For examples of Boc deprotection (in N-Boc compounds) with TMSOTf and TBDMSOTF, see ref 1
    • For examples of Boc deprotection (in N-Boc compounds) with TMSOTf and TBDMSOTF, see ref 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.