(3R,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol synthesis
- Product Name:(3R,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol
- CAS Number:252873-00-0
- Molecular formula:C6H10O3
- Molecular Weight:130.14
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
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Yield: 88 % ee
Reaction Conditions:
with hydrogenchloride in tetrahydrofuran;water at 20;
Steps:
25 Example 25; Synthesis of (3R,3AR,6AS)-hexahydrofuro[2,3-b]furan-3-ol (Compound (XXVI))
(3R,4'R)-3-(2',2'-Dimethyl-[1',3']dioxolane-4'-yl)tetrahydrofuran-2-ol (13.8 g) obtained in Example 24 was dissolved in THF (120 ML), and 6N hydrochloric acid (4 ML) was added.The mixture was stirred overnight at room temperature.anhydrous potassium carbonate (25 g) was added to the reaction mixture and the mixture was filtered.The concentrated residue was dissolved in toluene (20 ML) with heating and diisopropyl ether (30 ML) was added.The mixture was stirred at room temperature and the resulting crystals were collected by filtration and dried to give the title compound (2.8 g, 88% ee), which was almost a pure syn-form. 1H-NMR(CDCl3, δppm): 1.67-1.75(1H, m), 1.95-2.05(1H (-OH), br), 2.13-2.23(1H, m), 2.79-2.84(1H, m), 3.81-3.91(3H, m), 3.98(1H, dd, J=10 Hz, J=3 Hz), 4.23(1H, d, J=3 Hz), 5.89(1H, d, J=5 Hz).
References:
Sumika Fine Chemicals Co., Ltd. US2004/162340, 2004, A1 Location in patent:Page/Page column 30
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252873-00-0
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![(3S,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol](/CAS/GIF/156928-10-8.gif)
156928-10-8
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![3S-(3a,3a,6a)]-Hexahydrofuro[2,3-b]furan-3-ol Acetate](/CAS/GIF/162020-29-3.gif)
162020-29-3
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![tetrahydrofuro[2,3-b]furan-3(2H)-one](/CAS/20180713/GIF/445389-44-6.gif)
445389-44-6
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252873-00-0
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