Reaktion #7483

ord-565d90381b814599892f25d706657501

Reaktionsgleichung

Cc1[nH][nH]c(=O)c1Cc1ccc(OC(C)C)cc1
4-[(4-isopropoxyphenyl)methyl]-5-methyl-1,2-dihydro-3H-pyrazol-3-one
CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
acetobromo-α-D-glucose
→
CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole
Ausbeute 39.0%

Edukte

—
4A
Cc1[nH][nH]c(=O)c1Cc1ccc(OC(C)C)cc1
4-[(4-isopropoxyphenyl)methyl]-5-methyl-1,2-dihydro-3H-pyrazol-3-one
CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
acetobromo-α-D-glucose

Reagenzien

O=C([O-])[O-].[Ag+2]
silver carbonate

Lösungsmittel

C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Temperatur
65°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)

Vorschrift

To a suspension of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-1,2-dihydro-3H-pyrazol-3-one (46 mg), acetobromo-α-D-glucose (99 mg) and 4A molecular sieves in tetrahydrofuran (3 mL) was added silver carbonate (66 mg), and the mixture was stirred at 65° C. overnight under light shielding. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran), and successively by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1) to give 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (42 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087579B2uspto-grants-2006_08