1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 1-(3-O-Benzyl-5-O-(4,4'-dimethoxytrityl)-4-C-(p-toluenesulphonyloxymethyl)-beta-D-Xylofuranosyl)thymine

HRID 6779

Reaction equation

HRID 6779 reaction equation
[CH2:1]([O:8][C@H:9]1[C@@:13]([CH2:16][O:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])([CH2:14][OH:15])[O:12][C@@H:11]([N:28]2[CH:36]=[C:34]([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[C@@H:10]1[OH:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][O:39][C:40]1[CH:61]=[CH:60][C:43]([C:44](Cl)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[CH:42][CH:41]=1>N1C=CC=CC=1.ClCCl>[CH2:1]([O:8][C@H:9]1[C@@:13]([CH2:16][O:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])([CH2:14][O:15][C:44]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)[C:43]2[CH:42]=[CH:41][C:40]([O:39][CH3:38])=[CH:61][CH:60]=2)[O:12][C@@H:11]([N:28]2[CH:36]=[C:34]([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[C@@H:10]1[OH:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)2×HCID 106738211-(3-O-Benzyl-4-C-(p-Toluenesulphonyloxymethyl)beta-D-xylofuranosyl)thymine

Product 1

HCID 106530721-(3-O-Benzyl-5-O-(4,4'-dimethoxytrityl)-4-C-(p-toluenesulphonyloxymethyl)-beta-D-Xylofuranosyl)thymineYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of nucleoside 6 (3.66 g, 6.88 mmol) in anhydrous pyridine (25 cm3) was added N,N-(dimethylamino)pyridine (0.84 g, 6.81 mmol) and 4,4′-dimethoxytrityl chloride (3.5 g, 13.2 mmol) and the mixture was stirred for 23 h at room temperature. Additional N,N-(dimethylamino)pyridine (0.250 g, 2.06 mmol) and 4,4′-dimethoxytrityl chloride (0.700 g, 2.06 mmol) was added, and stirring was continued for 36 h at room temperature. Ice cold H2O (50 cm3) was added and the reaction mixture was diluted with dichloromethane (150 cm3). The organic phase was separated and washed with saturated aqueous solutions of sodium hydrogen carbonate (25 cm3×3) and brine (40 cm3×3), dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol/pyridine (0.75–1.5% methanol; 0.5% pyridine, v/v/v) as eluent to afford nucleoside 7 (4.28 g, 75%) as a white solid material after evaporation of the solvents under reduced pressure.

Workup

  1. stirringstirring
  2. waitwas continued for 36 h at room temperature
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous solutions of sodium hydrogen carbonate (25 cm3×3) and brine (40 cm3×3)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e288918a92354e2f82ef20876e9c4e95
Source dataset
uspto-grants-2006_08
Patent number
US07084125B2

Linked notes

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