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

HRID 1503306ノート

反応式

HRID 1503306 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 30088972',3'-Didehydro-3'-deoxy-4'-ethynylthymidine収率 94%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(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.

後処理

  1. customto form a uniform solution

出典と根拠

ORDレコード
ord-159b293b6c044f4a8e69bf52ddaa863c
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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