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Water → D-Glucitol, 1,5-anhydro-1-C-[5-(2-azulenylmethyl)-2-hydroxyphenyl]-, (1S)-

HRID 1376006
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인쇄 미리보기

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HRID 1376006 반응식
[Cl-].[Al+3].[Cl-].[Cl-].C1(OC)C=CC=CC=1.[CH:13]1[C:22]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:14]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:69]CC2C=CC=CC=2)=[C:28]([C@@H:30]2[O:59][C@H:58]([CH2:60][O:61]CC3C=CC=CC=3)[C@@H:49]([O:50]CC3C=CC=CC=3)[C@H:40]([O:41]CC3C=CC=CC=3)[C@H:31]2[O:32]CC2C=CC=CC=2)[CH:29]=1.O>C(Cl)Cl>[CH:13]1[C:22]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:14]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:69])=[C:28]([C@@H:30]2[O:59][C@H:58]([CH2:60][OH:61])[C@@H:49]([OH:50])[C@H:40]([OH:41])[C@H:31]2[OH:32])[CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 11535213HCID 11535213, 화합물

생성물 1

HCID 11560307D-Glucitol, 1,5-anhydro-1-C-[5-(2-azulenylmethyl)-2-hydroxyphenyl]-, (1S)-수율 30.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

Aluminum chloride (0.12 g) and anisole (4.0 ml) were added to a solution of (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-(benzyloxy)phenyl]-2,3,4,6-tetra-O-benzyl-D-glucitol (0.07 g) in methylene chloride (5 ml) and the mixture was stirred at room temperature for two hours. The reaction mixture was poured into ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-hydroxyphenyl]-D-glucitol (0.01 g).

후처리

  1. additionThe reaction mixture was poured into ice-
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

출처 및 근거

ORD 기록
ord-4f37995bf11d4aff81cb68901685cf40
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169761B2

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