1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 2'-Deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-methylthiouridine

HRID 722763Notes

Reaction equation

HRID 722763 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[S:12].[CH3:18][O:19][C:20]1[CH:41]=[CH:40][C:23]([C:24](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:22][CH:21]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([O:9][CH2:8][C@H:5]2[O:4][C@@H:3]([N:10]3[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]3=[S:12])[C@H:2]([CH3:1])[C@@H:6]2[OH:7])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:23]2[CH:40]=[CH:41][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 1317202082'-Deoxy-2'-methylthiouridine

Product 1

HCID 1317260662'-Deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-methylthiouridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 2′-deoxy-2′-methylthiouridine (1.09 g, 4 mmol) in dry pyridine (10 mL) was added 4,4′-dimethoxytritylchloride (1.69 g, 5 mmol) and 4-dimethylaminopyridine (50 mg) at room temperature. The solution was stirred for 12 hours and the reaction mixture quenched by adding MeOH (1 mL). The reaction mixture was concentrated under reduced pressure and the residue was dissolved in CH2Cl2 (100 mL), washed with saturated aqueous NaHCO3 (2×50 mL) and saturated aqueous NaCl (2×50 mL), and dried with MgSO4. The solution was concentrated under reduced pressure and the residue purified by silica gel (30 g) column chromatography. Elution with CH2Cl2—MeOH-triethylamine (89:1:1) furnished the title compound as a homogenous material. Pooling and concentrating the appropriate fractions furnished the 5′-O—DMT nucleoside as a foam (1.5 g, 66.5%).

Workup

  1. customthe reaction mixture quenched
  2. additionby adding MeOH (1 mL)
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in CH2Cl2 (100 mL)
  5. washwashed with saturated aqueous NaHCO3 (2×50 mL) and saturated aqueous NaCl (2×50 mL)
  6. dry with materialdried with MgSO4
  7. concentrationThe solution was concentrated under reduced pressure
  8. customthe residue purified by silica gel (30 g) column chromatography
  9. washElution with CH2Cl2—MeOH-triethylamine (89:1:1)

Sources & evidence

ORD record
ord-d14ba647ee784e4d99989259f55fc99b
Source dataset
uspto-grants-2006_11
Patent number
US07138517B2

Reaction notes

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