Reacción #577225

Ecuación de reacción

Sodium hydroxide

28

5-Acetylamino-4-(tert-butyldimethylsilanyloxy)-6-[(2,2-dimethyl-[1, 3]dioxolan-4-yl)-methoxycarbonylmethoxy-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

→

29

Rendimiento 70.0%

5-Acetylamino-4-(tert-butyldimethylsilanyloxy)-6-[carboxymethoxy-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid

Rendimiento 70.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic solvent was evaporated
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   Extracciónextract
4. 4
   Concentraciónwas concentrated

Procedimiento

Sodium hydroxide (5 mL, 0.1 M, 0.5 mmol) was added slowly to a stirred solution of 28 (100 mg, 0.19 mmol) in THF (5 mL). The resulting mixture was stirred for 2 h at room temperature. The organic solvent was evaporated and the aqueous solution was acidified with HCl to pH=2, extracted with ethyl acetate, and extract was concentrated to give 29 as a white solid (66 mg, 70%). mp 130° C. [α]D26+35.1° (c 1.2, CH3OH). 1H NMR (CD3OD, 500 MHz) 60.11 (s, 3H, CH3), 0.14 (s, 3H, CH3), 0.91 (s, 9H, 3CH3), 1.32 (s, 3H, CH3), 1.39 (s, 3H, CH3), 2.0 (s, 3H, NAc), 3.66 (s, 2H, OCH2), 3.98 (m, 2H), 4.14 (t, J=8.0 Hz, 1H), 4.20 (t, J=8.0 Hz, 1H), 4.27 (m, 1H, H-6), 4.33 (m, 1H), 4.63 (m, 1H, H-4), 5.84 (s, 1H, H-3). 13C NMR (CD3OD, 125 MHz) δ −4.65, −4.45, 18.81, 23.19, 25.43, 26.18, 26.61, 30.89, 51.97, 66.47, 68.13, 68.79, 70.76, 77.71, 78.38, 78.68, 109.35, 113.37, 144.93, 164.97, 173.24, 173.61. ESIMS calcd for C22H37NO10SiNa [M+Na]+ 526.3. Found 526.3. Anal. Calc. for C22H37NO10Si: C, 52.47; H, 7.41; N, 2.78. Found: C, 52.38; H, 7.48; N, 2.64.

Fuente