Benzene → 1-propenyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

HRID 2413044Notes

Reaction equation

HRID 2413044 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C:22](=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:16][C@@H:11]([O:12][CH2:13][CH:14]=[CH2:15])[C@@H:10]1[NH:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.C1C=CC=CC=1.N12CCN(CC1)CC2>C(Cl)(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].CC(C)=O.O>[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C:22](=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:16][C@@H:11]([O:12][CH:13]=[CH:14][CH3:15])[C@@H:10]1[NH:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 9237DabcoHCID 18595872Allyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Product 1

HCID 544293391-propenyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 4

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 500 mg. of Compound 6 in a mixture of 2.0 ml. of ethanol, benzene and water (7:3:1) 40 mg. of tris(triphenylphosphine)rhodium(I) chloride and 15 mg. of 1,4-diazabicyclo-[2.2.2]octane were added. The reaction mixture was heated under reflux overnight. Thin layer chromatography (5% acetone in CHCl3) showed the reaction to be complete. The reaction was conducted in the general manner described by Corey et al, in J. Org. Chem., 38 (1973) 3224 and P. A. Gent et al, J. Chem. Soc., Chem. Commun., (1974) 277-278. A high yield of Compound 7 was obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customthe reaction

Sources & evidence

ORD record
ord-9f71ab1a46774860b95d66d044bec2b9
Source dataset
uspto-grants-1985_01
Patent number
US04495346

Reaction notes

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