p=M140Search Result

Molecules 2000, 5, M140

(4R)-1'-Acetyl-2,3-O-isopropylidene-methylspiro [4,6-dideoxy-ß-D-ribo-hexopyranosid-4,5'-imidazolidin]-2',4'-dione

Bohumil Steiner, Jan Gajdos and Miroslav Koos*

Institute of Chemistry, Slovak Academy of Sciences, Dubravska 9, SK-84238 Bratislava, Slovakia Tel. +421-7-59410254, Fax +421-7-59410222 (E-mail: [email protected])

Received: 17 January 2000 / Accepted: 7 February 2000 / Published: 23 February 2000

Acetylation of hydantoins (imidazolidin-2,4-diones) and their 5-substituted derivatives normally occurs more readily in the 1-position [1]. A mixture of (4R)-2,3-O-isopropylidene-methylspiro[4,6-dideoxy-ß-D-ribo -hexopyranosid-4,5'-imidazolidin]-2',4'-dione [2] (0.86 g, 3 mmol), acetic anhydride (2.5 ml) and dry pyridine (5 ml) was heated at 50 °C for 8 h followed by concentration and co-evaporation with toluene under diminished pressure to give the crude product. This was purified on a column of silica gel using CHCl₃/MeOH 4:1 as an eluent. The fractions with R_f 0.35 were collected and evaporated to afford the title compound (0.87 g, 89%) as a colourless oil which solidified on standing.

M.p. 98-99 °C.

[a]_D 8° (c = 10 mg.cm³, methanol).

TLC (CHCl₃/MeOH 4:1, silica gel) R_f0.35.

¹H-NMR (CDCl₃): 5.26 (q, J=6.5 Hz, 1H, H-5); 4.54 (d, J=7.3 Hz, 1H, H-1); 4.37 (d, J=5.7 Hz, 1H, H-3); 4.27 (dd, J=7.3 and 5.7 Hz, 1H, H-2); 3.56 (s, 3H, OMe); 2.58 (s, 3H, COMe); 1.53 and 1.33 (2s, 2 x 3H, CMe₂); 1.27 (d, J=6.5 Hz, 3H, H-6).

¹³C-NMR (CDCl₃): 169.9, 169.5 and 153.5 (3 x C=O), 111.0 (CMe₂), 103.5 (C-1), 76.3 (C-2), 76.2 (C-3), 70.2 (C-4), 68.0 (C-5), 57.2 (OMe), 27.6 and 25.8 (CMe₂), 27.0 (COMe), 14.8 (C-6).

CI-MS (70 eV, pyridine): m/z 408 (100%, [M + C₅H₅NH]⁺).

Anal. calc. for C₁₄H₂₀N₂O₇ (328.32): C 51.22, H 6.14, N 8.53; found: C 51.11, H 6.18, N 8.59.

Acknowledgments: The authors would like to thank Scientific Grant Agency (VEGA, project No. 2/4144/99 and 2/7144/20) for financial support.

References

1. Theobald, R. S. In Rodd's Chemistry of Carbon Compounds, Second Edition, Coffey, S. and Ansell, M. F., Eds., Elsevier: Amsterdam, 1986; Vol. IV, Part C, p 191.

2. Koos, M.; Steiner, B.; Langer, V.; Gyepesova, D.; Durik, M. Carbohydr. Res., in press.

Sample availability: Available from authors.

1.	Theobald, R. S. In Rodd's Chemistry of Carbon Compounds, Second Edition, Coffey, S. and Ansell, M. F., Eds., Elsevier: Amsterdam, 1986; Vol. IV, Part C, p 191.
2.	Koos, M.; Steiner, B.; Langer, V.; Gyepesova, D.; Durik, M. Carbohydr. Res., in press.