Benzyl Alcohol → Benzyl 2-deoxy-beta-D-glucopyranoside

HRID 276096노트

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[O:1]=[CH:2][CH2:3][C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])[OH:5].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:1]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[CH2:3]1

참가 물질

반응물 2

HCID 244Benzyl Alcohol

HCID 1082232-Deoxyglucose2회

생성물 1

HCID 53805352Benzyl 2-deoxy-beta-D-glucopyranoside수율 69%

반응 조건

온도: 60 °C

실험 절차

2-deoxy-D-glucose (Compound 1a, 2.5 g, 15.2 mmol) was dissolved in benzyl alcohol (20 mL), and then Dowex® 50W-X8 (H+ form, 3.5 g) was added. The reaction solution was stirred at 60° C. for 24 hours. Then the resin was filtered off, and the product was purified by flash column chromatography with CHCl3—MeOH (15:1) to give Compound 1 (2.67 g, 10.5 mmol) in 69 percent yield.

후처리

addition(H+ form, 3.5 g) was added
filtrationThen the resin was filtered off
customthe product was purified by flash column chromatography with CHCl3—MeOH (15:1)

출처 및 근거

ORD 기록: ord-fb178818687e467dbdc84d38697bac2b
출처 데이터셋: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06353095B1

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