Acetic Acid → HCID 23541573, compound

HRID 1793296Notes

Reaction equation

S(=O)(=O)(O)O.CO[C@@H:8]1[O:30][C:29]([CH2:41][O:42][C:43](=[O:50])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH2:31][O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:19]([O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:9]1[O:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:51]([OH:54])(=[O:53])[CH3:52]>C(OC(=O)C)(=O)C.C(OCC)(=O)C.O>[C:51]([O:54][C@@H:8]1[O:30][C:29]([CH2:41][O:42][C:43](=[O:50])[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([CH2:31][O:32][C:33](=[O:40])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@@H:19]([O:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:9]1[O:10][C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:53])[CH3:52]

Participants

Conditions

Temperature: 25 °C

Procedure

Sulfuric acid (97%, 75 mL) was added to a solution of 1-O-methyl-2,3,5-tri-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-ribofuranose (1.7 g, 2.8 mmoles) in a mixture of acetic acid (6.7 mL) and acetic anhydride (0.67 mL) at 0° C. The reaction mixture was stirred at 25° C. for 15 h and diluted with ethyl acetate (50 mL) and water (10 mL). This solution 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 subjected to silica gel chromatography [ethanol (0–2%) in dichloromethane] to give 1.4 g of the titled compound as a white solid.

Workup

washThis solution was washed with brine (3 times), with a saturated aqueous solution of sodium bicarbonate
dry with materialdried over sodium sulfate
filtrationfiltered
customthe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-1fe3f07cdc4946e3899738f226f57903
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081449B2

Reaction notes

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