Réaction #577225

Équation de réaction

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

Rendement 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

Rendement 70.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe organic solvent was evaporated
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Extractionextract
4. 4
   Concentrationwas concentrated

Mode opératoire

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.

Source