반응 #577225

반응 방정식

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

수율 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

수율 70.0%

용매

THF

반응 조건

후처리

1. 1
   기타The organic solvent was evaporated
2. 2
   추출extracted with ethyl acetate
3. 3
   추출extract
4. 4
   농축was concentrated

실험 절차

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.

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