Triphenylphosphine → HCID 86760917, compound

HRID 227213Notes

Reaction equation

HRID 227213 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:29][CH2:28][C@@H:27]([N:30]=[N+]=[N-])[CH2:26][C@@H:25]2[OH:33])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1C=CC=CC=1.N>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([O:22][CH2:23][C@H:24]2[O:29][CH2:28][C@@H:27]([NH2:30])[CH2:26][C@@H:25]2[OH:33])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:35][CH:34]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 867609156-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-azido-2,3-dideoxy-D-mannitol

Product 1

HCID 86760917HCID 86760917, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 1049PyridineSolvent

Procedure

6.5 g (13.7 mmole) of 6-O-DMT-1,5-anhydro-2-azido-2,3-dideoxy-D-mannitol (5) were dissolved in 70 ml of pyridine and 50 ml of 32% aqueous ammonia, then 6.1 g (23.3 mmole) of triphenylphosphane are added. The reaction mixture was stirred for 18 h at r.t. Thereafter the reaction mixture was evaporated. The residue was dissolved in 400 ml of ethyl acetate und washed twice with 200 ml of 5% sodium hydrogencarbonate solution. Organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness. The residue was dissolved in 10 ml of ethyl acetate and purified by flash-chromatography over silica gel (ethyl acetate/methanol/1% triethylamine gradient). Product fractions were combined, evaporated and dried at high vacuum to yield 5.7 g (93%) of a colorless foam.

Workup

  1. customThereafter the reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in 400 ml of ethyl acetate
  3. washund washed twice with 200 ml of 5% sodium hydrogencarbonate solution
  4. customOrganic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in 10 ml of ethyl acetate
  9. custompurified by flash-chromatography over silica gel (ethyl acetate/methanol/1% triethylamine gradient)
  10. customevaporated
  11. customdried at high vacuum

Sources & evidence

ORD record
ord-7605df41ef8b430b9d9b9671d7381e22
Source dataset
uspto-grants-2009_07
Patent number
US07560231B2

Reaction notes

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