Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside synthesis
- Product Name:Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside
- CAS Number:78185-64-5
- Molecular formula:C22H24O6
- Molecular Weight:384.43
Yield:78185-64-5 89%
Reaction Conditions:
with pyridine at 0 - 20; for 16 h;
Steps:
2.2 Synthesis of compound 3
To a solution of (2R,3S,5S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol 1 (110 g, 0.746 mol, 1 eq) in pyridine (660 mL) was added p-toluoyl chloride (247.4 g, 1.6 mol, 2.15 eq) at 0 °C. The reaction mixture was allowed to warm to room temperature and stirred for a further 16 hours. Water (1 L) was added and the mixture extracted with DCM (3 x 300 mL). The combined organic extracts were then washed with a saturated NaHCC3 solution (2x 500 mL), 2N HC1 (2 x 500 mL), brine (500 mL), dried over Na2SO4 and then concentrated in vacuo to give (2R,3S,5S)-5-methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate as an brown oil (253 g, 89 %).
References:
WO2022/81739,2022,A1 Location in patent:Page/Page column 32-33
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