반응 #1755515

ord-ccb6dbfe7be04861b63b808bfd41ab91

반응 방정식

CCOOC(=C=O)[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O
1-(benzyloxycarbonyl)-3-(6-O-ethoxy-carbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-5-methylpyrazole
CCOC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O
3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxy-phenyl)methyl]-5-methyl-1H-pyrazole
수율 150.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The resulting insoluble material was removed by filtration
  2. 2
    기타the solvent of the filtrate was removed under reduced pressure
  3. 3
    기타The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

실험 절차

To a solution of 1-(benzyloxycarbonyl)-3-(6-O-ethoxy-carbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-5-methylpyrazole (0.17 g) in tetrahydrofuran (4 mL) was added 10% palladium-carbon powder, and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hours. The resulting insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxy-phenyl)methyl]-5-methyl-1H-pyrazole (0.10 g).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07989424B2uspto-grants-2011_08