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

HRID 1503305ノート

反応式

HRID 1503305 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-07a19624f4794565a60639f039b0b26e
出典データセット
uspto-grants-2015_12
特許番号
US09212174B2

反応ノート

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