Ethyl Acetate → 1-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl-]4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

HRID 1645304Notes

Reaction equation

HRID 1645304 reaction equation
[C:1]([Si:5]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[O:6][CH:7]1[C:11]([CH2:14][OH:15])([CH2:12][OH:13])[O:10][CH:9]([N:16]2[CH:21]=[CH:20][C:19](=[O:22])[NH:18][C:17]2=[O:23])[CH:8]1[OH:24])([CH3:4])([CH3:3])[CH3:2].[C:37](Cl)(C1C=CC=CC=1)([C:46]1[CH:53]=[CH:52][C:49]([O:50][CH3:51])=[CH:48][CH:47]=1)[C:38]1[CH:45]=[CH:44][C:41]([O:42][CH3:43])=[CH:40][CH:39]=1.C(O[CH2:65][CH3:66])(=O)C>N1C=CC=CC=1>[CH3:51][O:50][C:49]1[CH:48]=[CH:47][C:46]([CH:37]([C:38]2[CH:39]=[CH:40][C:41]([O:42][CH3:43])=[CH:44][CH:45]=2)[O:13][CH:12]([C:66]2[CH:65]=[CH:9][CH:8]=[CH:7][CH:11]=2)[C:11]2([CH2:14][OH:15])[O:10][CH:9]([N:16]3[CH:21]=[CH:20][C:19](=[O:22])[NH:18][C:17]3=[O:23])[CH:8]([OH:24])[CH:7]2[O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:53][CH:52]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 667727291-[4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Product 1

HCID 1317280501-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl-]4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Preferential protection with DMT at the α-hydroxymethyl position is performed following a published literature procedure (Nomura, M., et. al., J. Med. Chem. 1999, 42, 2901-2908). Generally, a solution of Compound 11 (1 eq.) in anhydrous pyridine is treated with DMTCl (1.3 eq.), then stirred at room temperature for several hours. Subsequently, the mixture is poured into ethyl acetate, washed with water, dried over anhydrous Na2SO4, filtered, and evaporated. Purification by silica gel chromatography will yield Compound 12.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-2c48dbb9b6c94a9c9b6e54a4583bc28a
Source dataset
uspto-grants-2012_02
Patent number
US08124745B2

Reaction notes

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