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Hydrochloric Acid → HCID 11989086, 화합물

HRID 909815
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HRID 909815 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

HCID 11989086HCID 11989086, 화합물수율 80.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b924413430124f17bf1409088d72ed84
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017792B2

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