Triphenylphosphine → HCID 18632083, compound

HRID 621754Notes

Reaction equation

HRID 621754 reaction equation
[C:1]([O:9][CH2:10][C:11]1([O:45][C@H:44]([CH2:46]O)[C@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:24]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:14]1[O:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:67]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:9][CH2:10][C:11]1([O:45][C@H:44]([CH2:46][I:67])[C@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:24]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:14]1[O:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 120273N-IodosuccinimideHCID 18632084HCID 18632084, compound

Product 1

HCID 18632083HCID 18632083, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (16 ml) was dissolved methyl 1,3,4,5-tetra-O-benzoyl-D-ido-2-heptulopyranoside (950 mg). To the solution were added triphenyl phosphine (1.65 g) and N-iodosuccinimide (1.2 g). The mixture was stirred at room temperature overnight. To the mixture was added ice-water (100 ml). The resulting oily substance was subjected to extraction with ethyl acetate. The ethyl acetate extract was washed with saturated sodium thiosulfate solution, 2N hydrochloric acid and saturated sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was chromatographed on a column of silica gel (200 ml) with toluene-ethyl acetate (10:1). The eluate was concentrated to dryness under reduced pressure to give a white powder (780 mg) of methyl 1,3,4,5-tetra-O-benzoyl-7-deoxy-7-iodo-D-ido-2-heptulopyranoside.

Workup

  1. extractionThe resulting oily substance was subjected to extraction with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with saturated sodium thiosulfate solution, 2N hydrochloric acid and saturated sodium hydrogencarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was chromatographed on a column of silica gel (200 ml) with toluene-ethyl acetate (10:1)
  7. concentrationThe eluate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a4c9412c3f5c4afaa54a503647f7c5fa
Source dataset
uspto-grants-1989_04
Patent number
US04824943

Reaction notes

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