Hydrochloric Acid → HCID 11989086, compound

HRID 909815Notes

Reaction equation

HRID 909815 reaction equation
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

Participants

5

Reactant 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

Product 1

HCID 11989086HCID 11989086, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-b924413430124f17bf1409088d72ed84
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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