Methanol → 2',3'-Didehydro-3'-deoxy-4'-ethynylthymidine

HRID 1503306노트

반응식

HRID 1503306 반응식
C(OC([O:8][CH2:9][C@@:10]1([C:24]#[C:25][Si](C)(C)C)[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CO.O>C(#N)C>[C:24]([C@:10]1([CH2:9][OH:8])[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)#[CH:25]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 53372553(2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran

생성물 1

HCID 30088972',3'-Didehydro-3'-deoxy-4'-ethynylthymidine수율 94%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(2R,5R)-5-t-Butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran (35 mg) was added to a glass reactor, and the atmosphere of the reactor was changed to nitrogen. To the reactor, potassium carbonate (72 mg) and methanol (3.5 mL) were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was mixed with water and acetonitrile so as to form a uniform solution, and the solution was quantitated (LC). The yielded compound was found to be 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine (yield: 94%, calculated through quantitation) (internal standard: methyl phthalate). The 1H-NMR data of the compound are as follows.

후처리

  1. customto form a uniform solution

출처 및 근거

ORD 기록
ord-159b293b6c044f4a8e69bf52ddaa863c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212174B2

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