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 1629691Notes

Reaction equation

HRID 1629691 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-a96c0c1484ce446f92f45d72d43ff578
Source dataset
uspto-grants-2014_07
Patent number
US08791083B2

Reaction notes

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