2H-Pyran-3(6H)-one, 2-(acetyloxy)-6-(acetyloxy)methyl-, (2R-trans)- synthesis
- Product Name:2H-Pyran-3(6H)-one, 2-(acetyloxy)-6-(acetyloxy)methyl-, (2R-trans)-
- CAS Number:71021-12-0
- Molecular formula:
- Molecular Weight:0
37112-31-5
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![2H-Pyran-3(6H)-one, 2-(acetyloxy)-6-[(acetyloxy)methyl]-, (2S-cis)- (9CI)](/CAS/20210305/GIF/82916-44-7.gif)
82916-44-7
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Yield:33.333 % de
Reaction Conditions:
with zinc(II) chloride at 20; for 3 h;Overall yield = 83 percent; Overall yield = 4.5 g;
Steps:
1,6-Di-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranos-2-ulose (6a) and 1,6-di-O-acetyl-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (6b).
Levoglucosenone (3), 3.0 g (24.2 mmol), was dissolvedin 15.0 mL of acetic anhydride, 3.3 g (24.2 mmol) ofZnCl2 was added, and the mixture was stirred at roomtemperature for for 3 h (TLC). The mixture wasneutralized with a saturated aqueous solution ofNaHCO3 (pH 6.0) and extracted with ethyl acetate(3×15.0 mL). The extract was dried over MgSO4, thesolvent was distilled off, and the residue was subjectedto silica gel chromatography. Yield 4.5 g (83%, a mixtureof α- and β-diastereoisomers 6a and 6b at a ratioof 2:1), caramel-like material, Rf 0.56 (petroleumether-EtOAc, 1:1). 1H NMR spectrum, δ, ppm: 1.97 s(3H, CH3), 2.00 s (3H, CH3), 2.02 s (3H, CH3), 2.08 s(3H, CH3), 4.11-4.19 m (1H, 6′-H), 4.29-4.35 m (1H,6-H), 4.71-4.79 m (1H, 5-H), 6.00 s (1H, 1-H), 6.18-6.23 m (1H, 4-H), 6.95-7.09 m (1H, 3-H). 13C NMRspectrum, δC, ppm: 20.6 (COCH3), 20.6, 20.7, 20.9,64.8 [64.2] (C6), 71.4 [68.1] (C5), 89.4 [89.3] (C1),126.56 [126.31] (C3), 147.0 [147.5] (C4), 168.9(COCH3), 170.4 [170.6] (COCH3), 187.0 [186.7] (C2).Found, %: C 52.59; H 5.27. C10H12O6. Calculated, %:C 52.63; H 5.30.
References:
Faizullina, L. Kh.;Galimova, Yu. S.;Khalilova, Yu. A.;Valeev [Russian Journal of Organic Chemistry,2021,vol. 57,# 7,p. 1047 - 1052][Zh. Org. Khim.,2021,vol. 57,# 7,p. 942 - 948]
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