Diethyl Ether → 2,3,4-Tri-o-benzoyl-l-rhamnono-1,5-lactone

HRID 2104224Notes

Reaction equation

HRID 2104224 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]([O:20][C@@H:21]1[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([O:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:25]([CH3:46])[O:24][CH:22]1[OH:23])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOCC>C(Cl)Cl>[C:12]([O:20][C@@H:21]1[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([O:37][C:38](=[O:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@H:25]([CH3:46])[O:24][C:22]1=[O:23])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 110708012,3,4-tri-O-benzoyl-L-rhamnopyranoseHCID 178418287HCID 178418287, compound

Product 1

HCID 112368422,3,4-Tri-o-benzoyl-l-rhamnono-1,5-lactoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

PCC (30 g, 0.139 mmol) and well-dried 4 Å molecular shives (25 g) are added into a flask under N2 current. Dry CH2Cl2 (250 ml) is added to the flask and the flask is stirred for 1 hour at a room temperature and cooled to 0° C. The compound (VI) (16 g, 33.6 mmol) dissolved in dry CH2Cl2 (250 ml) is added to and stirred 4 hours at a room temperature. The reaction is finished with adding cool Et2O (200 ml) and filtered by silica gel. The solvent is vacuum concentrated, and then the compound (VII) (13.54 g, 85%) is isolated using flash column chromatography (toluene/EtOAc, 10:1, v/v).

Workup

  1. additionare added into a flask under N2 current
  2. temperaturecooled to 0° C
  3. additionis added to and
  4. stirringstirred 4 hours at a room temperature
  5. additionwith adding
  6. filtrationfiltered by silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ec7f22c60e043689040467891bfbae6
Source dataset
uspto-grants-2009_08
Patent number
US07576225B2

Reaction notes

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