ACETAGASTRODINE synthesis
- Product Name:ACETAGASTRODINE
- CAS Number:64291-41-4
- Molecular formula:C21H26O11
- Molecular Weight:454.42
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Yield: 53.2%
Reaction Conditions:
with cesium hydroxide;N-benzyl-N,N,N-triethylammonium chloride in water;chlorobenzene at 60; for 4.5 h;
Steps:
Synthesis of 4-(hydroxymethyl)phenyl -D-glucopyranoside 2,3,4,6-tetraacetate
A solution of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2, 12.30 g, 30 mmol)in 120 mL chlorobenzene was added to a solution of 4-hydroxybenzyl alcohol (3, 7.44 g, 60mmol), CsOH (8.99 g, 60 mmol) and triethylbenzylammonium chloride (5.4 g, 24 mmol) in100 mL H2O. The mixture was then stirred at 60 °C for 4.5 h, after which it was cooled toroom temperature and the chlorobenzene layer separated, washed with 80 mL saturatedK2CO3 solution, 80 mL H2O and dried over anhydrous Na2SO4. The filtrate was concentratedunder vacuum to give a yellowish syrupy crude product 4, which was purified by crystallizationfrom 95 % ethanol to afford the desired compound 4 as a white solid. Yield: 53.2 %.
References:
Li, Yu-Wen;Ma, Cui-Li [Journal of the Serbian Chemical Society,2016,vol. 81,# 1,p. 23 - 28]
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