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Acetic acid 3-acetoxy-5-(5-formylamino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-isopropoxycarbonyloxy-tetrahydro-furan-2-ylmethyl ester

Acetic acid 2-acetoxymethyl-5-(5-formylamino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-isopropoxycarbonyloxy-tetrahydro-furan-3-yl ester

HOAc

→

59

수율 78.4%

Acetic acid 2-acetoxymethyl-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-isopropoxycarbonyloxy-tetrahydro-furan-3-yl ester

수율 78.4%

용매

MeOH

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실험 절차

Acetic acid 3-acetoxy-5-(5-formylamino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-isopropoxycarbonyloxy-tetrahydro-furan-2-ylmethyl ester (58) (420 mg, 0.84 mmol) was dissolved in MeOH (8.4 mL), cat. HOAc, and heated to 85° C. for 2 days. The reaction mixture was reduced to an oil in vacuo then subjected to flash chromatography (10-80% EtOAc-hexanes) yielding 310 mg (78%) of 59 as a pure white solid: 1HNMR (400 MHz, DMSO-d6) δ 8.37 (1H, s), 6.88 (2H, bs), 5.91-5.98 (2H, m), 5.47 (1H, dd, J1=5.2 Hz, J2=8.3 Hz), 4.65 (1H, septet, J=6.2 Hz), 4.46-4.51 (1H, m), 4.28 (1H, dd, J1=4.2 Hz, J2=11.9 Hz), 4.18 (1H, dd, J1=7.8 Hz, J2=11.6 Hz), 2.11 (3H, s),2.00 (3H, s), 1.16 (3H, d, J=6.3 Hz), 1.12 (3H, d, J=6.2 Hz).

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