Sodium Carbonate → 3'-O-(t-butyldimethylsilyl)thymidine

HRID 3652Notes

Reaction equation

HRID 3652 reaction equation
COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Si:39]([O:38][C@@H:25]1[C@@H:24]([CH2:23][OH:22])[O:28][C@@H:27]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:26]1)([C:42]([CH3:45])([CH3:43])[CH3:44])([CH3:40])[CH3:41]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 108760643'-O-(t-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)thymidine

Product 1

HCID 4538443'-O-(t-butyldimethylsilyl)thymidineYield 92.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5 g (7.6 mmol) 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl) thymidine 17 in 100 ml 80% aq. acetic acid was stirred until the removal of dimethoxytrityl group was completed. Saturated Na2CO3 was then added to adjust the pH of the solution to 6-7. The solution was then extracted with ethyl acetate. The extract was dried and the mixture was chromatographed on a silica gel column (CH2Cl2 :MeOH=20:1) to give 2.5 g of 3'-O-(tert-butyldimethylsilyl) thymidine 18 (92.6%).: m.p.93=20 -95° C. (lit. 83°-84° C.); H NMR (200 MHz CDCl3) δ9.18 (s, 1H, NH), 7.36 (b, 1H, H-6), 6.12 (t, J=6.8 Hz, 1H, H-1'), 4.44-4.48 (m, 1H, H-3'), 3.69-3.91 (m, 3H, H-4', H-5'), 2.87 (m, 1H, OH), 2.15-2.35 (m, 2H, H-2'), 1.87 (s, 3H, C=CMe), 0.86 (s, 9H, CMe3), 0.05 (s, 6H, SiMe2); 13C NMR (125 MHz, CDCl3) δ163.9 (C-4), 150.4 (C-2), 137.1 (C-6), 110.9 (C-5), 87.6 (C-4'), 86.8 (C-1'), 71.5 (C-3'), 61.9 (C-5'), 40.4 (C-2'), 25.7 (SiCMe3), 17.9 (SiCMe), 12.5 (C=CMe), -4.7 (SiMe2), -4.9 (SiMe2).

Workup

  1. extractionThe solution was then extracted with ethyl acetate
  2. customThe extract was dried
  3. customthe mixture was chromatographed on a silica gel column (CH2Cl2 :MeOH=20:1)

Sources & evidence

ORD record
ord-e89884540c3943e9884cf23c9919b30f
Source dataset
uspto-grants-1998_03
Patent number
US05734041

Reaction notes

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