Tetrabutylammonium nitrite - acetic anhydride system, tetrabutylammonium nitrite, tetrabutylammonium acetate, and cesium acetate - 18-crown-6 for efficient unmasking of alkyl N-phenylcarbamates

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5583-5586

  Akai, Shoji ^a   Nishino, Noriaki ^a   Iwata, Yukihiro ^a   Hiyama, Jun Ichi ^a   Kawashima, Etsuko ^b   Sato, Ken Ichi ^a   Ishido, Yoshiharu ^b  

^a KANAGAWA UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Carbamates; Carbohydrates; Cleavage reactions; Protecting groups

Indexed keywords

ACETIC ANHYDRIDE; CARBAMIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL ANALYSIS; COLUMN CHROMATOGRAPHY; NITROSATION; NUCLEAR MAGNETIC RESONANCE; NUCLEOTIDE METABOLISM; PURIFICATION; SPECTROSCOPY;

EID: 0032581673     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01126-5     Document Type: Article

References (12)

1. 1. a) Wolfrom, M. L. and Pletcher, D. E., J. Am. Chem. Soc., 1940, 62, 1151-1153;
2. b) Agarwal, K. L. and Khorana, H. G., J. Am. Chem. Soc., 1972, 94, 3578-3585.
3. 2. a) Bouveng, H. O., Acta Chem. Scand., 1961, 15, 87-95;
4. b) Bouveng, H. O., Acta Chem. Scand., 1961, 15, 96-100.
5. 3. Pirkle, W. H. and Hauske, J. R., J. Org. Chem., 1977, 42, 2781-2782.
6. 4. Greene, T. W. and M. Wuts, P. G., "Protective Groups in Organic Synthesis", John Wiley & Sons, Inc., 1990, Chart 2, p. 418.
7. 5. Nishino, S.; Nagato, Y.; Hasegawa, Y.; Yamamoto, H.; Kamaike, K. and Ishido, Y., Heteroatom Chem., 1991, 2, 187-196.
8. 6. White, E. H., J. Am. Chem. Soc., 1955, 77, 6008-6010.
9. 2 = -5.00): δ +210.9 [CON(NO)Ph] and -97.5 [CON(NO)Ph].
10. 8. The result suggests that the reaction might involve a considerable degree of N-denitrosation to the starting alkyl N-phenylcarbamate other than the objective unmasking reaction.
11. 2O (10 to 8 mol equiv.) gave 3 (60% yield) and its acetate, 4 to 1.5 mol equiv. gave 3 (39% yield), and 4 to (1.5 + 1.2) mol equiv. gave 3 (77% yield).
12. 10. Elemental analyses of the substrates and products gave satisfactory results for their structures assigned.