2,4,6-Trimethylpyridine → Methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl)-2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

HRID 466905

반응식

HRID 466905 반응식
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:14]([CH2:33][OH:34])[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([O:38][C@H:39]1[C@@H:44]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:43][C@H:42](Cl)[C@H:41]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@H:40]1[O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)(=[O:37])[CH3:36].CC1C=C(C)C=C(C)N=1>CCOCC.Cl([O-])(=O)(=O)=O.[Ag+]>[C:35]([O:38][C@H:39]1[C@@H:44]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:43][C@H:42]([O:34][CH2:33][C@H:14]2[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:16]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@H:15]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:41]([O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C@H:40]1[O:63][CH2:64][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)(=[O:37])[CH3:36]

참가 물질

6

반응물 3

HCID 79532,4,6-TrimethylpyridineHCID 11190476Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranosideHCID 544033654-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride

생성물 1

HCID 53849711Methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl)-2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

시약·촉매·용매 2

HCID 24562Silver perchlorate촉매HCID 3283Diethyl Ether용매

반응 조건

온도
-30 °C

실험 절차

Ethereal silver perchlorate (0.08 M, 76.9 mL, 6.15 mmol) is added with stirring at -30° C. to a solution of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside (2.078 g, 4.48 mmol), 4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl chloride (2.859 g, 5.6 mmol) and 2,4,6-trimethylpyridine (0.81 mL, 6.15 mmol) in ether (20 mL). The mixture is stirred 15 min at -30° C. and silver chloride precipitated. The mixture is filtered through a celite pad, the solids are washed with ether, the filtrate is concentrated under reduced pressure. The residue is dissolved in methylene chloride and the organic layer is washed successively with aqueous sodium thiosulfate and water. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure so as to afford a foam. Flash chromatography on silica gel and elution with a graded mixture of hexane and ethyl acetate will afford methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside as a foam.

후처리

  1. customsilver chloride precipitated
  2. filtrationThe mixture is filtered through a celite pad
  3. washthe solids are washed with ether
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washthe organic layer is washed successively with aqueous sodium thiosulfate and water
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure so as
  10. customto afford a foam
  11. washFlash chromatography on silica gel and elution
  12. additionwith a graded mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-ea2e577b99044a9fbcce7033137ab7e9
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157116

연결된 노트

불러오는 중…