1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione
1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione
Synthesis of 1-({[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione (1)
GC analysis (assay of 1, heptylbenzene as an internal standard): DB-17 (0.25 mmφ × 30 m, 0.25 μm), flow rate = 2.4 mL/min, injection mode; split (1/50), injection temperature; 180 °C, column temperature; 110 °C (15 min) → 10 °C/min → 280 °C (8 min), detection temperature; 280 °C (FID), retention time; 8.5 min (heptylbenzene), 31.9 min (major diastereomer of 1), 32.0 min (minor diastereomer of 1).
HPLC analysis (optical purity): CHIRALPAK IA-3 (4.6 mm*250 mm, 3 μm), hexane/0.01% THF solution of TFA = 45:55, flow rate = 0.5 mL/min, detector; UV 254 nm, retention time; 9.3 min (minor), 11.9 min (major).
1H NMR (400 MHz, CDCl3) δ 5.75 (1H, d, J = 4.8 Hz), δ 5.25 (1H, dt, J= 8.4, 6.0 Hz), δ 4.11 (1H, dd, J = 10.4, 6.4 Hz), δ 4.03 (1H, td, J = 8.8, 2.4 Hz), δ 3.97–3.91 (2H, m), δ 3.17–3.10 (1H, m), δ 2.86 (4H, s), δ 2.17–2.12 (1H, m), δ 2.04–1.93 (1H, m);
13C NMR (100 MHz, CDCl3) δ 168.4, 151.1, 109.1, 79.6, 69.9, 69.6, 45.0, 25.9, 25.4;
HRMS (ESI-HESI+) calcd for C11H17N2O7: 289.1030 ([M + NH4]+), found: 289.1028 ([M + NH4]+).
Research and Development of an Efficient Synthesis of a Key Building Block for Anti-AIDS Drugs by Diphenylprolinol-Catalyzed Enantio- and Diastereoselective Direct Cross Aldol Reaction
Health & Crop Sciences Research Laboratory, Sumitomo Chemical Co., Ltd., 1-21, Utajima 3-chome, Nishiyodogawa-ku, Osaka 555-0021, Japan
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.6b00178
*E-mail address: ikemotot2@sc.sumitomo-chem.co.jp.
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