t-Butylammonium fluoride → 3-Benzyloxymethyl-3'-benzyloxymethylthymidine

HRID 353609Notes

Reaction equation

HRID 353609 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:49](=[O:50])[C:48]([CH3:51])=[CH:47][N:12]([C@@H:13]2[O:37][C@H:17]([CH2:18][O:19][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[C@@:15]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([OH:16])[CH2:14]2)[C:11]1=[O:52])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([NH3+])(C)(C)C>C1COCC1>[CH2:1]([O:8][CH2:9][N:10]1[C:49](=[O:50])[C:48]([CH3:51])=[CH:47][N:12]([C@@H:13]2[O:37][C@H:17]([CH2:18][OH:19])[C@@:15]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([OH:16])[CH2:14]2)[C:11]1=[O:52])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21866379t-Butylammonium fluorideHCID 697536313-benzyloxymethyl-3'-benzyloxymethyl-5'-O-tert-butyldiphenylsilylthymidine

Product 1

HCID 697539423-Benzyloxymethyl-3'-benzyloxymethylthymidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-benzyloxymethyl-3′-benzyloxymethyl-5′-O-tert-butyldiphenylsilylthymidine (20 g, 28 mmol) in THF (200 ml) was treated with tert-butyl ammonium fluoride 1 M/THF (40 ml, 40 mmol) at room temperature for 16 hrs. The solution was concentrated in vacuo and the resulting oil chromatographed on silica gel (EtOAc/hexane, 7/3→8/2) to afford the product, 10 g (75%). m.p. 83-84° C.; 1H NMR (CDCl3), 1.92 (s, 3H, C5-CH3), 2.20-2.50 (m, 3H, C2′H, C5′OH), 3.73 (dd, 1H, C5′HH), 3.89 (dd, 1H, C5′HH), 4.09 (m, 1H, C4′H), 4.49 (m, 1H, C3′H) 4.62 (s, 2H, OCH2Ph), 4.70 (s, 2H, OCH2Ph), 4.81 (s, 2H, OCH2O), 5.49 (s, 2H, NCH2O), 6.19 (t, 1H, C1′H), 7.26-7.37 (m, 5H, CH═,ArH). Anal. Calcd. for C26H30N2O7: C, 64.94; H, 6.26; N, 5.75. Found: C, 64.71; H, 6.27; N, 5.81.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe resulting oil chromatographed on silica gel (EtOAc/hexane, 7/3→8/2)
  3. customto afford the product, 10 g (75%)

Sources & evidence

ORD record
ord-317dc952d44f4f89a8fa7895985b37fc
Source dataset
uspto-grants-2004_06
Patent number
US06753423B1

Reaction notes

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