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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Water → (2R,3R,4S,5R)-2-{2-[(Benzylsulfonyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268371
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HRID 2268371 반응식
[CH2:1]([S:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20]2)=[C:12]([NH:29][CH2:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[OH:45].[Na+].OOS([O-])=O.[K+].ClCCl.[OH2:58]>CC(C)=O.C(OCC)(=O)C>[CH2:1]([S:8]([CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20]2)=[C:12]([NH:29][CH2:30][CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:11]=1)(=[O:45])=[O:58])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

8

반응물 5

HCID 962Water2회HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59975291(2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

생성물 1

HCID 9809405
(2R,3R,4S,5R)-2-{2-[(Benzylsulfonyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

(2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (100 mg, 0.17 mmol) (example 76) was dissolved in stirred acetone (3 ml) and solid sodium hydrogen carbonate (100 mg, 1.2 mmol) added. A solution of Oxone (trade mark) (potassium peroxymonosulphate) (410 mg, 0.68 mmol) dissolved in water (2 ml) was then added dropwise to the original solution over the course of 30 min. Dichloromethane (2 ml) was also added and the reaction mixture stirred at room temperature for 60 hr. The reaction mixture was then diluted with ethyl acetate (100 ml) and water (50 ml). The organic layer was separated, dried with anhydrous magnesium sulfate and the solvent removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:hexane (4:1) increasing in polarity to ethyl acetate:methanol (96:4). This gave the title compound (50 mg) as a gum. MS: 630 (MH+).

후처리

  1. additionwas then added dropwise to the original solution over the course of 30 min
  2. customThe organic layer was separated
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:hexane (4:1)
  7. temperatureincreasing in polarity to ethyl acetate:methanol (96:4)

출처 및 근거

ORD 기록
ord-42a6c80f78a14215bacd0abafd232d16
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326359B1

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