Triphenylphosphine → 6-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-amino-2,3-dideoxy-D-glucitol

HRID 227215Notes

Reaction equation

HRID 227215 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 867609186-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-azido-2,3-dideoxy-D-glucitol

Product 1

HCID 673943796-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-amino-2,3-dideoxy-D-glucitolYield 91%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 1049PyridineSolvent

Procedure

1.1 g (2.3 mmole) of 6-O-DMT-1,5-anhydro-2-azido-2,3-dideoxy-D-glucitol (12) were dissolved in 11 ml of pyridine and 9 ml of 32% aqueous ammonia, then 1.0 g (3.9 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 180 ml of ethyl acetate und washed twice with 100 ml of 5% sodium hydrogencarbonate solution. Organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness. The residue was dissolved in 5 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 0.94 g (91%) of a colorless foam.

Workup

  1. customThereafter the reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in 180 ml of ethyl acetate
  3. washund washed twice with 100 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 5 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-59db5bda3864480c836ae0ef5355f4a5
Source dataset
uspto-grants-2009_07
Patent number
US07560231B2

Reaction notes

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