Acetic Acid → 1-[4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

HRID 642933

Reaktionsgleichung

Reaktionsgleichung von HRID 642933
C=O.[OH-].[Na+].[C:5]([Si:9]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:10][CH:11]1[CH:15]([CH:16]=[O:17])[O:14][CH:13]([N:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][C:19]2=[O:25])[CH:12]1[O:26]C(=O)C)([CH3:8])([CH3:7])[CH3:6].[C:42](O)(=[O:44])C>O1CCOCC1>[C:5]([Si:9]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:10][CH:11]1[C:15]([CH2:42][OH:44])([CH2:16][OH:17])[O:14][CH:13]([N:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][C:19]2=[O:25])[CH:12]1[OH:26])([CH3:7])([CH3:6])[CH3:8]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 86594161Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-formyl-tetrahydro-furan-3-yl Ester

Produkt 1

HCID 667727291-[4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Hydroxymethylation of the 5′-aldehyde is performed as per the method of Cannizzaro which is well documented in the literature (Jones, G. H., et. al., J. Org. Chem. 1979, 44, 1309-1317). These conditions are expected to additionally remove the 2′-O-acetyl group. Generally, Briefly, formaldehyde (2.0 eq., 37% aq.) and NaOH (1.2 eq., 2 M) is added to a solution of Compound 10 in 1,4-dioxane. After stirring at room temperature for several hours, this mixture is neutralized with acetic acid, evaporated to dryness, suspended in methanol, and evaporated onto silica gel. The resulting mixture is added to the top of a silica gel column and eluted using an appropriate solvent system to give Compound 11.

Aufarbeitung

  1. customto additionally remove the 2′-O-acetyl group
  2. customevaporated to dryness
  3. customevaporated onto silica gel
  4. additionThe resulting mixture is added to the top of a silica gel column
  5. washeluted

Quellen und Nachweise

ORD-Eintrag
ord-06ada91244b84992a9a96ee57f14e80c
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696345B2

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