l-Rhamnopyranose tetrabenzoate → 2,3,4-tri-O-benzoyl-L-rhamnopyranose

HRID 2104223Notes

Reaction equation

HRID 2104223 reaction equation
C([O:9][CH:10]1[O:42][C@@H:41]([CH3:43])[C@H: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:11]1[O:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C1C=CC=CC=1>CO.C1COCC1>[C:13]([O:12][C@@H:11]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@@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@H:41]([CH3:43])[O:42][CH:10]1[OH:9])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 13917742l-Rhamnopyranose tetrabenzoate

Product 1

HCID 110708012,3,4-tri-O-benzoyl-L-rhamnopyranoseYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The compound (V) (22.4 g, 38.6 mmol) is dissolved in MeOH:THF (3:7, 400 ml), and then NH3 gas is bubbled for 15 minutes at 0° C. and stirred at 0° C. for 1 hour. The reaction process is identified by thin layer chromatography while repeating the above process. The solvent is vacuum concentrated, and then the compound (VI) (16 g, 87%, α:β=14:1) is isolated using flash column chromatography (toluene/EtOAc, 10:1, v/v).

Workup

  1. customNH3 gas is bubbled for 15 minutes at 0° C.
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d6e751faef0b4a84baeb34dcb3e9b388
Source dataset
uspto-grants-2009_08
Patent number
US07576225B2

Reaction notes

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