Acetic Acid → HCID 69663726, compound

HRID 1793297Notes

Reaction equation

HRID 1793297 reaction equation
S(=O)(=O)(O)O.[C:6]([O:14][C@@H:15]1[C@H:21]([O:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@:20]([CH3:41])([CH2:31][O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:19][C@H:16]1OC)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:42]([OH:45])(=[O:44])[CH3:43]>C(OC(=O)C)(=O)C.C(OCC)(=O)C.[Cl-].[Na+].O>[C:42]([O:45][C@@H:16]1[O:19][C@:20]([CH3:41])([CH2:31][O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:21]([O:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:15]1[O:14][C:6](=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)(=[O:44])[CH3:43]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 69663955HCID 69663955, compound

Product 1

HCID 69663726HCID 69663726, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

Concentrated sulfuric acid (97%, 99 mL) was added to a solution of 2,3,5-tri-O-benzoyl-1-O-methyl-4-C-methyl-β-D-ribofuranose (1.8 g, 3.6 mmoles) in a mixture of acetic acid (9.0 mL) and acetic anhydride (0.90 mL) at 0° C. The reaction mixture was stirred at 25° C. for 16 h and diluted with ethyl acetate (50 mL) and brine (10 mL). The organic extract was washed with brine (3 times), with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, filtered, and the filtrate was evaporated to dryness. The residue was dissolved with a mixture of ethyl acetate and hexanes (1:4, v/v) and the b anomer of the title compound crystallized instantaneously. The white crystals were filtered to give 1.1 g (56%) of the title compound in its pure b anomer form. The filtrate was subjected to silica gel chromatography [ethyl acetate (20%) in hexanes] to give 0.6 g (32%) of the titled compound as an oil (3:1 mixture of a/b anomers).

Workup

  1. extractionThe organic extract
  2. washwas washed with brine (3 times), with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved with a mixture of ethyl acetate and hexanes (1:4, v/v)
  7. customthe b anomer of the title compound crystallized instantaneously
  8. filtrationThe white crystals were filtered

Sources & evidence

ORD record
ord-d337e890f4ac46aea5a533793e1357af
Source dataset
uspto-grants-2006_07
Patent number
US07081449B2

Reaction notes

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