1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → N2-isobutyryl-5'-O-(tert-butyldimethylsilyl)-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosin

HRID 968366Notes

Reaction equation

HRID 968366 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:31])[C:10]2[N:11]=[CH:12][N:13]([C:29]=2[N:30]=1)[C@@H:14]1[O:28][C@H:18]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C@@H:16]([OH:17])[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:32][O:33][C:34]1[CH:55]=[CH:54][C:37]([C:38](Cl)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:36][CH:35]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:31])[C:10]2[N:11]=[CH:12][N:13]([C:29]=2[N:30]=1)[C@@H:14]1[O:28][C@H:18]([CH2:19][O:20][Si:21]([C:24]([CH3:26])([CH3:25])[CH3:27])([CH3:23])[CH3:22])[C@@H:16]([O:17][C:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:37]2[CH:36]=[CH:35][C:34]([O:33][CH3:32])=[CH:55][CH:54]=2)[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 1359094375'-O-TBDMS-N2-ibu-dG

Product 1

HCID 136334533N2-isobutyryl-5'-O-(tert-butyldimethylsilyl)-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosinYield 698.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Conditions

Temperature
40 °C

Procedure

N2-isobutyryl-5′-O-(tert-butyldimethylsilyl)-2′-deoxyguanosine (19.8 g) was dissolved in 100 ml of anhydrous pyridine. 4,4′-dimethoxytrityl chloride (1.66 g) was added to the resultant solution and 140 ml of anhydrous pyridine was further added, follow by stirring at 40° C. After the reaction completed, the reaction mixture was neutralized by sodium hydrogen carbonate and pyridine was distilled off. Extraction using chloroform was carried out and the extract was washed by a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. The extract was concentrated and purified by column chromatography (ethyl acetate/hexane) to obtain 25.8 g of the titled compound (yield: 78%).

Workup

  1. additionwas further added
  2. distillationwas distilled off
  3. extractionExtraction
  4. washthe extract was washed by a saturated aqueous solution of sodium chloride
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationThe extract was concentrated
  7. custompurified by column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-13b4fedb11f54c1a9810978186b2bf22
Source dataset
uspto-grants-2005_10
Patent number
US06958391B2

Reaction notes

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