1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 6-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-azido-2,3-dideoxy-D-mannitol

HRID 227212Notes

Reaction equation

HRID 227212 reaction equation
[N:1]([C@H:4]1[CH2:9][C@H:8]([OH:10])[C@@H:7]([CH2:11][OH:12])[O:6][CH2:5]1)=[N+:2]=[N-:3].[CH3:13][O:14][C:15]1[CH:36]=[CH:35][C:18]([C:19](Cl)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C:19]([O:12][CH2:11][C@H:7]2[O:6][CH2:5][C@@H:4]([N:1]=[N+:2]=[N-:3])[CH2:9][C@@H:8]2[OH:10])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:18]2[CH:35]=[CH:36][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 86760916HCID 86760916, compound

Product 1

HCID 867609156-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-azido-2,3-dideoxy-D-mannitolYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

7.6 g (44 mmole) of 1,5-anhydro-2-azido-2,3-dideoxy-D-mannitol (4) were coevaporated with 3×40 ml of pyridine and then dissolved in 120 ml of pyridine. Thereafter, 19.6 g (53.3 mmole) of 4,4′-dimethoxytritylchloride in 120 ml of pyridine are added at r.t. within 1 h under stirring. The reaction mixture was stirred for another 2 h at r.t. Then pyridine was evaporated and the residue was dissolved in 800 ml of ethyl acetate und washed twice with 400 ml of 5% sodium hydrogencarbonate solution. Organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness. The residue was dissolved in 30 ml of ethyl acetate and purified by flash-chromatography over silica gel (n-hexane/ethyl acetate/1% triethylamine gradient). Product fractions were combined, evaporated and dried at high vacuum to yield 15.8 g (77%) of a yellowish foam.

Workup

  1. stirringThe reaction mixture was stirred for another 2 h at r.t
  2. customThen pyridine was evaporated
  3. dissolutionthe residue was dissolved in 800 ml of ethyl acetate
  4. washund washed twice with 400 ml of 5% sodium hydrogencarbonate solution
  5. customOrganic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. dissolutionThe residue was dissolved in 30 ml of ethyl acetate
  10. custompurified by flash-chromatography over silica gel (n-hexane/ethyl acetate/1% triethylamine gradient)
  11. customevaporated
  12. customdried at high vacuum

Sources & evidence

ORD record
ord-587ea8f44b3c4759a02692eed9471c72
Source dataset
uspto-grants-2009_07
Patent number
US07560231B2

Reaction notes

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