Benzoyl chloride → HCID 86747468, compound
Reaction equation
C(OC[C@H]1OC(OC)(CO)[C@@H](O)C1)(=O)C1C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1.[C:30]([O:38][CH2:39][C@@:40]1([O:47][C@H:46]([CH2:48][O:49][C:50](=[O:57])[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:45][C@@H:43]1[OH:44])[O:41][CH3:42])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OC[C@]1(O[C@H](COC(=O)C2C=CC=CC=2)C[C@@H]1O)OC)(=O)C1C=CC=CC=1>ClCCl.N1C=CC=CC=1>[C:30]([O:38][CH2:39][C:40]1([O:47][C@H:46]([CH2:48][O:49][C:50](=[O:57])[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:45][C@@H:43]1[OH:44])[O:41][CH3:42])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
Conditions
- Temperature
- -40 °C
Procedure
To about 1 g of crude methyl 6-O-benzoyl-4-deoxy-α,β-D-fructofuranoside (prepared as described in Example 1, Step 6) in dichloromethane (25 mL) containing 4 Å molecular sieves and pyridine (0.28 mL) and maintained at -40° C., benzoyl chloride (0.4 mL) was added and the solution was stirred between -30° to -20° C. for 5 h. The reaction mixture was filtered, diluted with dichloromethane and washed with ice cold 0.5M HCl, sat. aqueous NaHCO3 solution, dried over magnesium sulfate and evaporated. Final purification was effected by chromatography on a column of silica gel. The yields of the separated anomers were 0.582 g of methyl 4-deoxy-1,6-di-O-benzoyl-α-D-fructofuranoside and 0.200 g of methyl 4-deoxy-1,6-di-O-benzoyl-β-D-fructofuranoside.
Workup
- filtrationThe reaction mixture was filtered
- additiondiluted with dichloromethane
- washwashed with ice cold 0.5M HCl, sat. aqueous NaHCO3 solution
- dry with materialdried over magnesium sulfate
- customevaporated
- customFinal purification
- customThe yields of the separated anomers
Sources & evidence
- ORD record
- ord-07a59f36f3054d3380a3a5cd8bf80264
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05276143
Reaction notes
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