REFERENCES
- Lutz , J. M. , Held , A. H. , Hottinger , M. , Hübscher , V. and Benner , A. S. 1996 . Nucleosides & Nucleotides , 24 : 1308
- Sauer , D. R. and Schneller , S. W. 1989 . ibid , 8 : 1079
- Prhavc , M. , Townsend , L. B. and Kobe , J. 1991 . ibid , 10 : 729
- Prhavc , M. and Kobe , J. 1996 . ibid , accepted
- Mohar , B. , Štimac , A and Kobe , J. 1993 . ibid , 12 : 793
- A mixture of tetrazole 4, Et3N (1.4 mole equiv.), and dimethyl 3-chloro-2-pentenedioate (1.2 mole equiv.) in THF is stirred at -5°C for 4 h, and concentrated. The residue is dissolved in EtOAc, washed with water, brine, and dried (Na2SO4). The concentrated residue is chromatographed on silica gel (eluent petroleum ether/ EtOAc 4:1) to furnish 5 as a light yellow syrup
- Light amber solid, m.p. = 214–5°C (from abs. ethanol). [α]d21 = -48.6 (c 0.5, H20). 1H NMR (299.94 MHz, D2O/ TMS): δ 1.51 (m, 1H, H-5′a), 2.29 (m, 2H, H-4′, H-5′b), 3.68 (m, 4H, CHaHbOH, H-7a, H-7b), 3.91 (m, 1H, H-1′), 3.99 (m, 1H, H-3′), 4.18 (m, 1H, H-2′) ppm. 13C NMR (75.43 MHz, Me2SO-d6): 30.07 (C-5′), 31.86 (br C-7), 40.57 (br C-l′), 46.89 (C-4′), 63.28 (CH2OH), 73.18 (C-3′), 75.55 (C-2′), 106.23 (C-3a), 148.60 and 149.33 (br C-3, br C-7a), 162.18 (C-4), 171.33 (br (C-6) ppm. IR (KBr): 3400 (NH, OH), 1704 (CO) cm−1. FABMS m/z 282 (MH+).