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

HRID 227214Notes

Reaction equation

HRID 227214 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 866726091,5-Anhydro-2-azido-2,3-dideoxy-D-glucitol

Product 1

HCID 867609186-O-(4,4'-Dimethoxytrityl)-1,5-anhydro-2-azido-2,3-dideoxy-D-glucitolYield 77.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

0.52 g (3.0 mmole) of 1,5-anhydro-2-azido-2,3-dideoxy-D-glucitol (11) were dissolved in 9 ml of pyridine. Thereafter, 1.1 g (3.2 mmole) of 4,4′-dimethoxytritylchloride in 9 ml of pyridine are added at r.t. within 30 min under stirring. The reaction mixture was stirred for another 3 h at r.t. Then pyridine was evaporated and the residue was dissolved in 100 ml of ethyl acetate und washed twice with 60 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 (n-hexane/ethyl acetate/1% triethylamine gradient). Product fractions were combined, evaporated and dried at high vacuum to yield 1.1 g (77%) of a colorless foam.

Workup

  1. stirringThe reaction mixture was stirred for another 3 h at r.t
  2. customThen pyridine was evaporated
  3. dissolutionthe residue was dissolved in 100 ml of ethyl acetate
  4. washund washed twice with 60 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 5 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-3d46dd64ace349cb83a7cee5a4baf389
Source dataset
uspto-grants-2009_07
Patent number
US07560231B2

Reaction notes

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