(2S,3S,5S)-5-(acetoxymethyl)-tetrahydrofuran-2,3-diyl diacetate synthesis
- Product Name:(2S,3S,5S)-5-(acetoxymethyl)-tetrahydrofuran-2,3-diyl diacetate
- CAS Number:865853-43-6
- Molecular formula:C11H16O7
- Molecular Weight:260.24
Yield:865853-43-6 870 mg
Reaction Conditions:
with sulfuric acid;acetic acid in methanol at 0; for 1 h;
Steps:
29.6
Step 6 : Preparation of compound 29g Acetic anhydride (6.51 mL, 68.9 mmol) and concentrated sulfuric acid (36.91 uL, 0.69 mmol) were added to a stirred solution of compound 29f (1.2 g, 6.89 mmol) in acetic acid (39.4 mL, 688.89 mmol) at 0 °C. After stirring for 1 h rt, the reaction mixture was quenched with cold water (100 mL), stirred for 30 min rt and extracted with ethyl acetate (3x 60 mL). The organic layer was successively washed with saturated aqueous sodium bicarbonate solution (3 x 90 mL), brine solution (2 x 90 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue (combined with silica gel: 4 g) was purified by flash column chromatography over silica (0%-40% EA in PE, V/V) to give compound 29g (870 mg) as a colorless oil. ’H NMR (400 MHz, CDB CN) d 6.03 (s, 1H), 5.11 id. J= 4.6 Hz, 1 1 1). 4.49 (dtd, J= 3.3, 6.5, 9.6 Hz, 1H), 4.19 (dd. ./ 3.3. 11.9 Hz, 1H), 4.00 (dd, J = 6.6, 12.0 Hz, 1H), 2.03 - 1.99 (m, 1 1 1 ).
References:
WO2019/118839,2019,A1 Location in patent:Page/Page column 227-228; 230
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