反応 #2358565

反応方程式

D-glucose

3,4,5-tribenzyloxybenzoic acid

EDC.HCl

→

product

収率 9.4%

β-D-Glucopyranose Pentakis[3,4,5-tris(phenylmethoxy)-benzoate]

収率 9.4%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux overnight
3. 3
   その他The cooled reaction mixture
4. 4
   抽出was then extracted with 1N HCl (3×), saturated NaHCO3 (2×), and brine (2×)
5. 5
   乾燥the organic layer was dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The resulting residue was purified by column chromatography over silica gel (75:24:1 CH2Cl2:toluene:ethyl acetate)

実験手順

A mixture of 1.17 mmol of D-glucose, 8.57 mmol of 3,4,5-tribenzyloxybenzoic acid, 10.68 mmol of EDC.HCl and 9.84 mmol of DMAP was suspended in 130 mL of CH2Cl2 and was heated at reflux overnight. The cooled reaction mixture was then extracted with 1N HCl (3×), saturated NaHCO3 (2×), and brine (2×), the organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by column chromatography over silica gel (75:24:1 CH2Cl2:toluene:ethyl acetate) to provide 0.253 g (9%) of product. 1H NMR (CDCl3, 400 MHz) δ 7.45-7.15 (m, 85H), 6.21 (d, J=8.0 Hz, 1H), 6.05 (t, J=10.0 Hz, 1H), 5.84 (dd, J=10.0, 8.0 Hz, 1H), 5.73 (t, J=10.0 Hz, 1H), 5.14-4.92 (m, 30H), 4.76 (m, 1H), 4.44 (m, 1H), 4.35 (m, 1H).

出典