4-(tert-Butyldimethylsilyloxy)benzylidene acetal: A novel benzylidene-type protecting group for 1,2-diols

Tetrahedron Letters

Volumn 45, Issue 19, 2004, Pages 3817-3821

  Kaburagi, Yosuke ^a   Osajima, Hiroyuki ^a   Shimada, Kousei ^a   Tokuyama, Hidetoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Benzylidene acetal; Deprotection under basic conditions; Diol; Hydroxylamine; Protecting group

Indexed keywords

4 (TERT BUTYLDIMETHYLSILYLOXY)BENZYLIDENE ACETAL; ACETAL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; DESILYLATION; HYDROLYSIS; STEREOCHEMISTRY;

EID: 1842839850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.065     Document Type: Article

References (8)

1. Green T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;Wiley, New York. p 201.
2. Shimada K., Kaburagi Y., Fukuyama T. J. Am. Chem. Soc. 125:2003;4048-4049.
3. Conversion of rather simple silyloxybenzylidene acetals to their corresponding aldehydes has been reported: Sabitha G., Babu R.S., Reddy E.V., Yadav J.S. Chem. Lett. 2000;1074.
4. Krishnaveni N.S., Surendra K., Reddy M.A., Nageswar Y.V.D., Rao K.R. J. Org. Chem. 68:2003;2018.
5. Sekine M., Hata T. J. Org. Chem. 48:1983;3011.
6. Tsunoda T., Suzuki M., Noyori R. Tetrahedron Lett. 21:1980;1357.
7. +, found 423.2571.
8. +, found 236.1239. Spectroscopic data for 22: see Ref. 2.