Thymine → (2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran

HRID 1503305Notes

Reaction equation

HRID 1503305 reaction equation
[C:1]([O:5][C:6]([O:8][CH2:9][C@@:10]1([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[O:14][C@@H:13](OC(OC(C)(C)C)=O)[CH:12]=[CH:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:29]1[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]1=[O:31]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[C:1]([O:5][C:6]([O:8][CH2:9][C@@:10]1([C:23]#[C:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[O:14][C@@H:13]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH:12]=[CH:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 1135ThymineHCID 53372552(2S,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-t-butoxycarbonyloxy-2,5-dihydrofuran

Product 1

HCID 53372553(2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuranYield 78.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

(2S,5R)-5-t-Butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-t-butoxycarbonyloxy-2,5-dihydrofuran (β/α=>99/1) (2.0 g) was added to a glass reactor, and the atmosphere of the reactor was changed to nitrogen. To the reactor, thymine (3.1 g) and N,N′-dimethylformamide (40 mL) were added under stirring. To the resultant mixture, tetrakis(triphenylphosphine)palladium(0) (560 mg) was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, and the residue was purified through silica gel column chromatography, to thereby yield 1.6 g of (2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran (yield: 78%, β/α=>99/1). The 1H-NMR data of the compound are as follows.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-07a19624f4794565a60639f039b0b26e
Source dataset
uspto-grants-2015_12
Patent number
US09212174B2

Reaction notes

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