(3aS, 6aR)-3-Oxyhexahydrofuro [2, 3-b] furan

(3aS, 6aR)-3-Oxyhexahydrofuro [2, 3-b] furan

809286-93-9 cas

[ Molecular Formula ]:	C6H8O3
[ Molecular Weight ]:	128.12600

(6): Under a nitrogen atmosphere, a, solution containing 440 mg (3.38 mmol) (3S, 3aS, 6aR)-3-hydroxy-hexahydrofuro [2, 3-b] furan (5), 599 mg (5.11 mmol) 4-methylmorpholine-N-oxide, and 2 g 4 A molecular sieves in CH₂Cl₂ (30 mL) was stirred for 20 minutes. Then, tetrapropylammonium perruthenate (36 mg (0.10 mmol)) was added at room temperature. After 5-10 minutes, the reaction mixture was filtered through a pad of silica gel (5 g) with CH₂Cl₂ (100 mL). After evaporation, column chromatography (silica gel 70 g, ethyl acetate in hexanes 40%) gave compound (6) (409 mg. 94%) as a colorless solid, R_f=0.3, [α]²⁵_D -126.6°, c 0.8, CHCl₃, 

IR (Neat) 1758, 1658, 1023 cm^-1;

 ¹H-NMR (400 MHz, CDCl₃) δ: 2.23 (m_c, 1H), 2.96 (dd, 1H, J=6.8 Hz, J=6.8 Hz), 3.79 (m_c, 1H), 3.99 (m, 1H), 4.11 (s, 2H), 6.02 (d, 1H, J=5.0 Hz).

 ¹³C-NMR (100.6 MHz, CDCl₃, Dept) δ: 30.38 (-), 49.58 (+), 67.65 (-), 71.69 (-), 107.89 (+), 215.52 (quat). 

C₆H₈O₃;

Exact Mass: 128.05; Mol. Wt.: 128.13; C, 56.24, H, 6:29, 0, 37.46.

https://www.google.com/patents/US20040127727

/////////////