Hydrogen Peroxide → 3'-Deoxy-3'-(3-hydroxypropyl)-5'-O-tert-butyldiphenylsilylthymidine

HRID 1489461Notes

Reaction equation

HRID 1489461 reaction equation
[CH2:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:28]2[CH:36]=[C:34]([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:5]1)[CH:2]=[CH2:3].O.C([O-])(O)=[O:39].[Na+].OO>C1COCC1>[OH:39][CH2:3][CH2:2][CH2:1][C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:7][C@@H:6]([N:28]2[CH:36]=[C:34]([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:5]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 516892Sodium BicarbonateHCID 154508083'-Deoxy-3'-allyl-5'-O-tert-butyldiphenylsilylthymidine

Product 1

HCID 228782693'-Deoxy-3'-(3-hydroxypropyl)-5'-O-tert-butyldiphenylsilylthymidineYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 37 (0.74 g, 2 mmol) was treated with BH3Me2S (0.388 g, 5.12 mmol) in THF (10 ml). The reaction mixture was quenched with MeOH (0.7 mL). H2O (3 mL) and NaHCO3 (1.11 g, 13.3 mmol) were added to the reaction mixture followed by H2O2 (30%, 1.91 mL, 16.92 mmol). After work-up, the residue was purified by silica gel chromatography. The product was crystallized from ether/hexane to furnish 0.41 g of the product as white needles. mp 150°-151° C.

Workup

  1. customThe reaction mixture was quenched with MeOH (0.7 mL)
  2. customAfter work-up, the residue was purified by silica gel chromatography
  3. customThe product was crystallized from ether/hexane

Sources & evidence

ORD record
ord-ff3ecc93bdf741088cdce2bd42720de2
Source dataset
uspto-grants-1997_10
Patent number
US05677437

Reaction notes

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