Hydrochloric Acid → 1-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine

HRID 6778

Reaction equation

HRID 6778 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH2:28][O:29]C(=O)C2C=CC=CC=2)([CH2:18][O:19]C(=O)C2C=CC=CC=2)[O:7][C@H:6]1[N:38]1[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]1=[O:40])(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@H:9]1[C:8]([CH2:18][OH:19])([CH2:28][OH:29])[O:7][C@@H:6]([N:38]2[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]2=[O:40])[C@@H:5]1[OH:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 107940411(2-O-Acetyl5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-beta-D-xylofuranosyl)thymineHCID 10942334Sodium Methoxide

Product 1

HCID 106910381-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of nucleoside 4 (9.00 g, 0.014 mol) in methanol (130 cm3) was added sodium methoxide (3.87 g, 0.0716 mol). The reaction mixture was stirred at room temperature for 4 h and then neutralised with dilute hydrochloric acid. The mixture was evaporated to dryness under reduced pressure followed by coevaporation using toluene (15 cm3×3). The residue was purified by silica gel column chromatography using dichloromethane/methanol (4–1 5% methanol, v/v) as eluent to give nucleoside triol 5 (4.82 g, 89%) as a white solid material after evaporation of the solvents under reduced pressure.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5bfff2d50122426db511b3e9f2d81ec6
Source dataset
uspto-grants-2006_08
Patent number
US07084125B2

Linked notes

Loading…