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Hydrochloric Acid → HCID 11989086、化合物

HRID 909815
ノート
印刷プレビュー

反応式

HRID 909815 の反応式
Cl.O1CCCC1.[CH2:7]([O:14][C@@H:15]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[S:18][C:16]1([C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([CH:54]2OCC[O:55]2)[CH:48]=1)[OH:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[CH2:7]([O:14][C@@H:15]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[S:18][C:16]1([C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([CH:54]=[O:55])[CH:48]=1)[OH:17])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 119890852,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(1,3-dioxolane-2-yl)phenyl]-5-thio-D-glucopyranose

生成物 1

HCID 11989086HCID 11989086、化合物収率 80.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Then, 6M hydrochloric acid (120 mL) was added to a tetrahydrofuran (50 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(1,3-dioxolane-2-yl)phenyl]-5-thio-D-glucopyranose (6.01 g, 8.12 mmol) while ice-cooled, and stirred at room temperature for two days. The reaction mixture was added with an iced water and extracted with ethyl acetate and the organic phase was washed with a saturated sodium bicarbonate aqueous solution, brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain colorless amorphous 2,3,4,6-tetra-O-benzyl-1-C-(4-chloro-3-formylphenyl)-5-thio-D-glucopyranose (4.53 g, 80%).

後処理

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washthe organic phase was washed with a saturated sodium bicarbonate aqueous solution, brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained
  7. customby evaporating the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-b924413430124f17bf1409088d72ed84
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017792B2

反応ノート

読み込み中…

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