alpha-D-Glucopyranosyl bromide, tetraacetate → 5-Methyl-4-{[4-(cyclopropylidenemethyl)-phenyl]methyl}-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole

HRID 7358

반응식

HRID 7358 반응식
[CH3:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16]2[CH2:18][CH2:17]2)=[CH:11][CH:10]=1.[CH3:19][C:20]([O:22][CH2:23][C@H:24]1[O:29][C@H:28](Br)[C@H:27]([O:31][C:32]([CH3:34])=[O:33])[C@@H:26]([O:35][C:36]([CH3:38])=[O:37])[C@@H:25]1[O:39][C:40]([CH3:42])=[O:41])=[O:21]>O1CCCC1.C(=O)([O-])[O-].[Ag+2]>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([O:7][C@@H:28]2[O:29][C@H:24]([CH2:23][O:22][C:20](=[O:21])[CH3:19])[C@@H:25]([O:39][C:40](=[O:41])[CH3:42])[C@H:26]([O:35][C:36](=[O:37])[CH3:38])[C@H:27]2[O:31][C:32](=[O:33])[CH3:34])[C:3]=1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[C:16]2[CH2:18][CH2:17]2)=[CH:13][CH:14]=1

참가 물질

5

반응물 2

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 219897045-Methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1,2-dihydro-3h-pyrazol-3-one

생성물 1

HCID 691337265-Methyl-4-{[4-(cyclopropylidenemethyl)-phenyl]methyl}-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole수율 16.2%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-one (0.026 g) and acetobromo-α-D-glucose (0.049 g) in tetrahydrofuran was added silver carbonate (0.036 g), and the mixture was stirred at 60° C. overnight under light shielding. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran) and successively by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3) to give 5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.010 g).

후처리

  1. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran) and successively by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3)

출처 및 근거

ORD 기록
ord-9ebaaf178676404ebfef3fc9396de50d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087579B2

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