HCID 18660663, compound → HCID 18660671, compound

HRID 1266902Notes

Reaction equation

HRID 1266902 reaction equation
[Si]([O:8][C@@H:9]1[C@:13]([C:15]#[C:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([OH:14])[C@@H:12]([CH2:27][OH:28])[O:11][C@H:10]1[N:29]1[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]1=[O:31])(C(C)(C)C)(C)C.Cl.CO>>[CH:18]([Si:17]([C:16]#[C:15][C@@:13]1([OH:14])[C@@H:12]([CH2:27][OH:28])[O:11][C@@H:10]([N:29]2[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]2=[O:31])[C@@H:9]1[OH:8])([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:22])[CH3:23])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 18660663HCID 18660663, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 18660671HCID 18660671, compoundYield 89%

Procedure

Added to 2.0 g of 1-(2-O-(tert-butyldimethylsilyl)-3-C-triisopropylsilylethynyl-β-D-ribofuranosyl)uracil obtained above were 50 of a 2.6% (w/v) hydrochloric acid/methanol solution, and the mixture was stirred at room temperature. After 180 minutes, the solvent was distilled off under reduced pressure, and the residue was azeotropically distilled with ethanol, purified by column chromatography on covered silica gel (chloroform:methanol=50:1-15:1) and then suspended in hexane. The suspension was filtered to obtain 1.4 g (yield: 89%) of the title compound as a white powdered substance.

Workup

  1. customobtained
  2. distillationthe solvent was distilled off under reduced pressure
  3. distillationthe residue was azeotropically distilled with ethanol
  4. custompurified by column chromatography on covered silica gel (chloroform:methanol=50:1-15:1)
  5. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-2680fa6d3d7246fb9e84159ffbd1dd08
Source dataset
uspto-grants-2003_04
Patent number
USRE038090E1

Reaction notes

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