Potassium Phosphate, Tribasic → methyl 2-[2(3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]phenyl)ethyl]azulene-1-carboxylate

温度

50 °C

A THF solution (8.0 ml) of 9-borabicyclo[3.3.1]nonane was added to (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-(3-vinylphenyl)-D-glucitol (1.0 g) and the mixture was refluxed with heating for four hours. Next, a 3 M aqueous solution of potassium phosphate (1.3 ml) and DMF (12 ml) were added to the reaction mixture. Methyl 2-chloroazulene-1-carboxylate (0.35 g) and 1,1′-diphenylphosphinoferrocene dichloropalladium (II) (0.12 g) were further added to the mixture, followed by stirring at 50° C. for two hours. After cooling to room temperature, the reaction mixture was poured into ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated brine in that order and dried over anhydrous sodium sulfate. The reaction mixture was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain methyl 2-[2(3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]phenyl)ethyl]azulene-1-carboxylate (0.88 g).

1. temperaturethe mixture was refluxed
2. temperaturewith heating for four hours
3. temperatureAfter cooling to room temperature
4. additionthe reaction mixture was poured into ice-
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated brine in that order
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationThe reaction mixture was concentrated
9. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

ORDレコード

ord-d12ab9dd791f4990945ccb0b6dfacdee

出典データセット

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07169761B2