Selective deprotection of alkyl vs. aryl silyl ethers

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2495-2498

  Lipshutz, Bruce H ^a   Keith, John ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; DRUG TRANSFORMATION; MOLECULAR INTERACTION;

EID: 0032560041     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00381-5     Document Type: Article

References (10)

1. 1. Evans, D.A.; Dinsmore, C.J.; Ratz, A.M.; Evrard, D.A.; Barrow, J.C. J. Am. Chem. Soc. 1997, 119, 3417; Nicolaou, K.C.; Chu, X-J.; Ramanjulu, J.M.; Natarajan, S.; Brase, S.; Rubsam, F.; Boddy, C.N.C. Angew. Chem. Int. Ed. Engl. 1997, 36, 1539.
2. 1. Evans, D.A.; Dinsmore, C.J.; Ratz, A.M.; Evrard, D.A.; Barrow, J.C. J. Am. Chem. Soc. 1997, 119, 3417; Nicolaou, K.C.; Chu, X-J.; Ramanjulu, J.M.; Natarajan, S.; Brase, S.; Rubsam, F.; Boddy, C.N.C. Angew. Chem. Int. Ed. Engl. 1997, 36, 1539.
3. 2. Lipshutz, B.H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Letters 1997, 38, 753.
4. 3. Collington, E.W.; Finch, H.; Smith, I.J. Tetrahedron Letters 1985, 26, 681.
5. 4. Vaino, A.R.; Szarek, W.A. J. Chem. Soc., Chem. Commun.,1996, 2351.
6. 2/MeOH is ca. 5.
7. 6. Hallock, Y.F.; Manfredi, K.P.; Dai, J-R.; Cardellina, J.H.; Gulakowski, R.J.; McMahon, J.B.; Schaffer, M.; Stahl, M.; Gulden, K-P.; Bringmann, G.; Francois, G.; Boyd, M.R. J. Nat. Prod., 1997, 60, 677, and references therein.
8. 2 (ca 20%) as a co-solvent, which seems to have no effect on the efficiency of silyl ether cleavage.
9. 8. Cruickshank, F.R.; Benson, S.W. J. Phys. Chem. 1969, 73, 733.
10. 4, filtering, and evaporation to dryness gives material that was then purified by flash column chromatography.