HCID 18650251, compound → HCID 21309194, compound

HRID 443004Notes

Reaction equation

HRID 443004 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:13](C=O)([CH2:14][OH:15])[O:12][C@@H:11]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:27]([Mg]Br)=[CH2:28]>C1COCC1>[CH:27]([CH:14]([OH:15])[C@H:13]1[O:12][C@@H:11]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:10][C@@H:9]1[O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3])=[CH2:28]

Participants

4

Reactant 2

HCID 18650251HCID 18650251, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 21309194HCID 21309194, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3'-O-t-Butyldimethylsilyl thymidine 4'-aldehyde (5.0 g; azeotroped twice with toluene, 25 ml) was dissolved in dry THF (60 ml) and cooled to -78° C., followed by addition of 1.0M solution of vinylmagnesium bromide (2.5 eq.) in THF. The reaction mixture was stirred for 30 minutes and then quenched with saturated aqueous NH4Cl, diluted with ethyl acetate, washed with water (2×100 ml) and then with brine. Then the organic layer was dried. The title compound was purified by flash chromatography using 30% ethyl acetate/hexane, affording a 43% yield of the desired alcohol.

Workup

  1. customazeotroped twice with toluene, 25 ml)
  2. dissolutionwas dissolved in dry THF (60 ml)
  3. customquenched with saturated aqueous NH4Cl
  4. additiondiluted with ethyl acetate
  5. washwashed with water (2×100 ml)
  6. customThen the organic layer was dried
  7. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-251b045c7f864774bfc9e6dfd9247a54
Source dataset
uspto-grants-1999_04
Patent number
US05892024

Reaction notes

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