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

HRID 1629690
Notes
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Reaction equation

HRID 1629690 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-47219c4019d74dbd880a5d908886f72a
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes