Acetic Acid 5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl Ester → Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-yl Ester

HRID 1629688

Reaction equation

HRID 1629688 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)[O:10][CH:11](C2C=CC=CC=2)[CH:12]2[O:16][CH:15]([N:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]3=[O:24])[CH:14]([O:25][C:26](=[O:28])[CH3:27])[CH:13]2[O:29][Si:30]([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=CC=1>C(O)(=O)C>[C:43]([Si:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[O:29][CH:13]1[CH:12]([CH2:11][OH:10])[O:16][CH:15]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[NH:19][C:18]2=[O:24])[CH:14]1[O:25][C:26](=[O:28])[CH3:27])([CH3:44])([CH3:45])[CH3:46]

Participants

3

Reactant 1

HCID 131728049Acetic Acid 5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl Ester

Product 1

HCID 66774584Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-yl Ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 5′-O-DMT group is removed as per known literature procedures 4,4′-dimethoxytrityl ethers are commonly removed under acidic conditions (Oligonucleotides and analogues, A Practical Approach, Eckstein, F., ed, IRL Press, New York.) Generally, Compound 8 (1 eq.) is dissolved in 80% aqueous acetic acid. After several hours, the mixture is evaporated, dissolved in ethyl acetate and washed with a sodium bicarbonate solution. Purification by silica gel chromatography will give compound 9.

Workup

  1. customThe 5′-O-DMT group is removed as
  2. customare commonly removed under acidic conditions (Oligonucleotides and analogues
  3. waitAfter several hours
  4. customthe mixture is evaporated
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with a sodium bicarbonate solution
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c3ad35d1470648e9ac933e94b4b65c5d
Source dataset
uspto-grants-2014_07
Patent number
US08791083B2

Linked notes

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