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Volumn , Issue 10, 2007, Pages 1619-1621

Rapid access to in situ generated (R)- and (S)-2-furyloxirane and associated regioselective nucleophilic ring-opening studies

Author keywords

Epoxide; Furan; Nucleophilic ring opening; Regioselectivity; Umpolung effects

Indexed keywords

2 FURYLOXIRANE; ETHYLENE OXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 34347332463 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-980381 Document Type: Article

Times cited : (6)

References (22)

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- Although D-glucal is commercially available for large-scale reactions, the use of the cheaper peracetyl derivative is recommended
- Although D-glucal is commercially available for large-scale reactions, the use of the cheaper peracetyl derivative is recommended.

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10
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- f = 0.3) to obtain 2.1 g (82%).
- f = 0.3) to obtain 2.1 g (82%).

11
- 34347365238
- Synthesis of Compound 6 To a solution of 3 (2.1 g, 16.3 mmol) in pyridine (20 mL) was added TsCl (3.83 g, 20.6 mmol) and the reaction mixture was stirred over night at r.t. The whole mixture was poured onto a slurry of ice (300 mL) and coned HCl (ca. 10 mL, The resulting mixture was extracted with Et2O (200 mL) and the organic layer was washed with sat. NaHCO3 solution (50 mL, H2O (50 mL) and brine (50 mL, The organic layer was dried (MgSO4) and concentrated to approx. 60 mL. The so-prepared solution was used without further purification, but stored in the fridge over 4 Å MS (0.14 M, α] D20 +36.7 (c 4.01, Et2O, 1H NMR (300 MHz, CDCl3, δ, 7.79-7.75 (m, 2 H, 7.35-7.31 (m, 3 H, 6.32-6.30 (m, 2H, 4.95 (dd, 1 H, J, 4.4, 7.0 Hz, 4.31-4.19 (m, 2 H, 2.65 (br s, OH, 2.44 (s, 3 H, ppm. 13C NMR 75 MHz, CDCl3
- 5S: 305.0460; found: 305.0467. Note: Tosylate 6 is stable in solution and on silica gel, however, if concentrated at elevated temperatures (40-50°C) rapid polymerization occurs affording a dark-green gum. Analytical samples were obtained after column chromatography, concentration at 20°C and finally evaporation of the remaining solvent under high vacuum. Compound 6 is stable under argon for several hours in pure form.

12
- 34347356037
- 3a,9 whereas tosylate 6 is stable in the presence of benzylamine and even thioethane at r.t. as observed over 96 h.
- 3a,9 whereas tosylate 6 is stable in the presence of benzylamine and even thioethane at r.t. as observed over 96 h.

13
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- (2006) Tetrahedron: Asymmetry , vol.17 , pp. 2154
- Tannis, S.P.¹ Evans, B.R.² Nieman, J.A.³ Parker, T.T.⁴ Taylor, W.D.⁵ Heasley, S.E.⁶ Herrinton, P.M.⁷ Perrault, W.R.⁸ Hohler, R.A.⁹ Dolak, L.A.¹⁰ Hester, M.R.¹¹ Seest, E.P.¹²

14
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- 2O/pyridine, formation of the L-glucosyl bromide with HBr/AcOH followed by elimination with zinc dust achieved 53% overall yield. Following the procedure for L-galactal: (a) Litjens, R. E. J. N.; den Heeten, R.; Timmer, M. S. M.; Overkleeft, H. S.; van der Marel, G. A. Chem. Eur. J. 2005, 11, 1010.
- 2O/pyridine, formation of the L-glucosyl bromide with HBr/AcOH followed by elimination with zinc dust achieved 53% overall yield. Following the procedure for L-galactal: (a) Litjens, R. E. J. N.; den Heeten, R.; Timmer, M. S. M.; Overkleeft, H. S.; van der Marel, G. A. Chem. Eur. J. 2005, 11, 1010.

15
- 34347341213
- 3): δ = 170.4, 170.2, 169.4, 145.5, 98.9, 73.8, 67.3, 67.1, 53.3, 20.8, 20.6, 20.6 ppm.
- 3): δ = 170.4, 170.2, 169.4, 145.5, 98.9, 73.8, 67.3, 67.1, 53.3, 20.8, 20.6, 20.6 ppm.

16
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20
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21
- 34347344547
- Representative Experimental Procedure and Characterization Data for Selected Compounds To a solution of 6 (5.0 mL, 0.71 mmol, 0.14 M) in Et2O7 was added NaH (2 equiv, 60 mg, 60% in mineral oil) under an argon atmosphere at r.t. After 30 min a solution of Li-TBS-dithiane13 (1.2 equiv) in anhyd THF (2 mL) containing HMPA (0.7 mL) was added at r.t. The reaction was quenched after 2 h with sat. NH 4Cl solution (10 mL) and extracted with Et2O (20 mL, The organic layer was washed with H2O (10 mL, brine (10 mL, dried (MgSO4, and evaporated. The residue was further purified by column chromatography on silica gel (PE-EtOAc, 50:1) affording 8 (122 mg, 50, Rf, 0.5) and 9 (81 mg, 33, Rf, 0.41, Compound 8: [α]D20, 77.0 (c 0.5, CHCl3, 1H NMR 300 MHz, CDCl3, δ
- 3): δ = 152.8, 142.3, 110.4, 107.4, 63.0, 45.6, 24.7, 14.8 ppm.

22
- 0034596854
- The product from this reaction has been previously characterized; our data agree with the previously published: Blake, A. J, Cunningham, A, Ford, A, Teat, S. J, Woodward, S. Chem. Eur. J. 2000, 6, 3586
- The product from this reaction has been previously characterized; our data agree with the previously published: Blake, A. J.; Cunningham, A.; Ford, A.; Teat, S. J.; Woodward, S. Chem. Eur. J. 2000, 6, 3586.

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