Hydrochloric Acid → 1-(3,5-Di-O-benzyl-beta-D-Allofuranosyl)Thymine

HRID 6784Notes

Reaction equation

HRID 6784 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@@H:8]([C@@H:18]([CH2:27][O:28]C(=O)C2C=CC=CC=2)[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@H:6]1[N:37]1[CH:45]=[C:43]([CH3:44])[C:41](=[O:42])[NH:40][C:38]1=[O:39])(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@@H:9]1[C@@H:8]([C@@H:18]([CH2:27][OH:28])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@@H:6]([N:37]2[CH:45]=[C:43]([CH3:44])[C:41](=[O:42])[NH:40][C:38]2=[O:39])[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 105557771-(2-O-Acetyl-6-O-Benzoyl-3,5-Di-O-benzyl-beta-D-Allofuranosyl)ThymineHCID 10942334Sodium Methoxide

Product 1

HCID 108380101-(3,5-Di-O-benzyl-beta-D-Allofuranosyl)Thymine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of nucleoside 15 (3.00 g, 4.88 mmol) in methanol (50 cm3) was added sodium methoxide (0.79 g, 14.7 mmol). The reaction mixture was stirred for 14 h at room temperature and subsequently neutralised with dilute hydrochloric acid (5 cm3) whereupon ice-cold H2O (50 cm3) was added. The resulting mixture was extracted using ethyl acetate (3×100 cm3) and the combined organic phase was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (98.5:1.5, v/v) as eluent to give nucleoside 16 as white solid material (2.00 g, 88%) after evaporation of the solvents under reduced pressure.

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted
  3. customthe combined organic phase was evaporated to dryness under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a99ac7b5da104cf58c343a9f780e764c
Source dataset
uspto-grants-2006_08
Patent number
US07084125B2

Reaction notes

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