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Ethanol → Benzyl 2-Deoxy-2-phthalimido-beta-D-glucopyranoside

HRID 466977
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인쇄 미리보기

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HRID 466977 반응식
C([O:4][C@H:5]1[C@H:18]([O:19]C(=O)C)[C@@H:17]([CH2:23][O:24]C(=O)C)[O:16][C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:6]1[N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(=O)C.C(OCC)(=O)C.C(O)C.CCCCCC>CO.C[O-].[Na+]>[C:29]1(=[O:38])[N:28]([C@@H:6]2[C@@H:5]([OH:4])[C@H:18]([OH:19])[C@@H:17]([CH2:23][OH:24])[O:16][C@H:7]2[O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 8058HexaneHCID 8857Ethyl AcetateHCID 11237799(2R,3S,4R,5R,6R)-2-(Acetoxymethyl)-6-(benzyloxy)-5-(1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyran-3,4-diyl diacetate

생성물 1

HCID 14727657Benzyl 2-Deoxy-2-phthalimido-beta-D-glucopyranoside수율 89.4%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 10942334Sodium Methoxide용매

실험 절차

Benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (6) (40.6 g, 84 mM) in 750 ml of dry methanol and 30 ml of 0.5M sodium methoxide was added to a 2 liter round bottomed flask equipped with magnetic stirring bar, septum inlet and bent tube adapter and the contents stirred at room temperature for 18 hours. TLC indicated completion of the reaction. (The TLC solvent was 10:2:10 ethyl acetate: ethyl alcohol:hexane). To the mixture was added 15 g of Bio-Rad (Bio-Rad Laboratories, P.O. Box 708, 220 Maple Ave., Rockville Center, NY 11571) ion exchange resin AG-50W-X-8 (prewashed with H2O, methanol, and dried) and stirred for 5 minutes (pH should be≤7.0). The mixture, after filtration followed by the removal of solvent, furnished benzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (7), 30 g (89.4% yield).

후처리

  1. customequipped with magnetic stirring bar, septum inlet
  2. customcompletion of the reaction
  3. additionTo the mixture was added 15 g of Bio-Rad (Bio-Rad Laboratories, P.O. Box 708, 220 Maple Ave., Rockville Center, NY 11571) ion exchange resin
  4. dry with material(prewashed with H2O, methanol, and dried)
  5. stirringstirred for 5 minutes (pH should be≤7.0)
  6. filtrationThe mixture, after filtration
  7. customfollowed by the removal of solvent

출처 및 근거

ORD 기록
ord-b5ef918c8be0457f97297c7e009fbc9b
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05158941

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