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

HRID 1503305노트

반응식

HRID 1503305 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-07a19624f4794565a60639f039b0b26e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212174B2

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