Phosphoric Acid → 3-Benzyloxymethyl-3'-benzyloxymethylthymidine-5'-aldehyde

HRID 353610Notes

Reaction equation

HRID 353610 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:32](=[O:33])[C:31]([CH3:34])=[CH:30][N:12]([C@@H:13]2[O:20][C@H:17]([CH2:18][OH:19])[C@@:15]([CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([OH:16])[CH2:14]2)[C:11]1=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.P(=O)(O)(O)[OH:52]>CS(C)=O>[CH2:1]([O:8][CH2:9][N:10]1[C:32](=[O:33])[C:31]([CH3:34])=[CH:30][N:12]([C@@H:13]2[O:20][C@H:17]([C:18](=[O:52])[OH:19])[C@@:15]([CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([OH:16])[CH2:14]2)[C:11]1=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 10868DicyclohexylcarbodiimideHCID 697539423-Benzyloxymethyl-3'-benzyloxymethylthymidine

Product 1

HCID 697522063-Benzyloxymethyl-3'-benzyloxymethylthymidine-5'-aldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-benzyloxymethyl-3′-benzyloxymethylthymidine (14.5 g, 30 mmol) in DMSO (200 ml) was treated with DCC (33 g, 160 mmol) and phosphoric acid 85% (2.0 g) for 16 h. The reaction mixture was filtered and concentrated in vacuo. The resultant oil was chromatographed on silica gel (EtOAc/hexane, 7/3) to afford the product as a viscous oil, 11 g (76%). 1H NMR (CDCl3) 1.92 (s, 3H, C5-CH3), 2.20-2.52 (m, 2H, C2′H), 4.09 (m, 1H, C4′H), 4.49 (m, 1H, C3′H), 4.62 (s, 2H, NCH2O), 6.28 (t, 1H, C1′H) 7.24-7.51 (M, 11H, ArH, CH═), 9.65 (s, 1H, CHO). Anal. Calcd. for C26H28N2O7: C, 64.99; H, 5.87; N, 5.83. Found: C, 64.68; H, 5.95; N, 6.01.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe resultant oil was chromatographed on silica gel (EtOAc/hexane, 7/3)

Sources & evidence

ORD record
ord-23c3631642684d48ad5d0d778f906ce0
Source dataset
uspto-grants-2004_06
Patent number
US06753423B1

Reaction notes

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