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

HRID 466977
ノート
印刷プレビュー

反応式

HRID 466977 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

HCID 14727657Benzyl 2-Deoxy-2-phthalimido-beta-D-glucopyranoside収率 89.4%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 10942334Sodium Methoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5ef918c8be0457f97297c7e009fbc9b
出典データセット
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05158941

反応ノート

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