Ozone → HCID 86701323, 화합물

A mixture of (2S,3S,4S)-3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran (0.621 g, 2.00 mmol) and NaHCO3 (17.0 mg, 0.200 mmol) in MeOH (0.22 ml) and DCM (7 mL) was treated with ozone at −78° C. until the solution became light blue in color. The mixture was purged with nitrogen until colorless, diluted with MeOH (7 mL), and treated with a solution of NaBH4 (0.454 g, 12.0 mmol) and NaOAc (0.335 g, 4.08 mmol) in H2O (7 mL). The mixture was slowly warmed to room temperature and stirred for 12 h. The mixture was diluted with EtOAc and washed with H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered, and the filtrate concentrated. The crude residue was purified by flash chromatography (SiO2, hexanes/EtOAc gradient) to yield the title compound as a colorless oil (0.590 g, 93%): IR (neat) 3389, 2876, 1453, 1064, 733, 696 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.39-7.27 (m, 10H), 4.64 (s, 2H), 4.63 (s, 2H), 4.06-3.97 (m, 1H), 3.92-3.83 (m, 1H), 3.80-3.73 (m, 2H), 3.47 (dd, J=6.2, 4.3 Hz, 1H), 2.92 (d, J=4.9 Hz, 1H), 2.23 (dd, J=6.9, 4.9 Hz, 1H), 1.24 (d, J=6.4 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 137.91, 137.71, 128.69, 128.62, 128.23, 128.19, 128.09, 81.72, 79.53, 73.63, 72.78, 67.66, 61.45, 19.74; ESIMS m/z 339.2 ([M+Na]+).

1. customThe mixture was purged with nitrogen until colorless,
2. additiondiluted with MeOH (7 mL)
3. washwashed with H2O
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with EtOAc
6. washThe combined organic phases were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthe filtrate concentrated
10. customThe crude residue was purified by flash chromatography (SiO2, hexanes/EtOAc gradient)

ORD 기록

ord-2b2a094799c24b2eabf637dcc869303d

출처 데이터셋

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09144239B2