Triethylamine → 2-[4-(2-hydroxyethyl)benzyl]-5-methoxyphenyl beta-D-glucopyranoside

HRID 1982853노트

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HRID 1982853 반응식
[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][O:30]COC)=[CH:24][CH:23]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][OH:30])=[CH:26][CH:27]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 688708525-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl beta-D-glucopyranoside

생성물 1

HCID 688718222-[4-(2-hydroxyethyl)benzyl]-5-methoxyphenyl beta-D-glucopyranoside수율 47.9%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

To a solution of 5-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl β-D-glucopyranoside (0.053 g) in methanol (2.3 mL) was added p-toluenesulfonic acid monohydrate (0.032 g), and the mixture was stirred at 50° C. for 3 hours. After cooling to room temperature, to the reaction mixture was added triethylamine (0.5 mL), and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give 2-[4-(2-hydroxyethyl)-benzyl]-5-methoxyphenyl β-D-glucopyranoside (0.023 g).

후처리

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

출처 및 근거

ORD 기록
ord-ca0e9f45270846bc84ad26ae212bd657
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541341B2

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