Triethylamine → 1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine

HRID 2181378ノート

反応式

HRID 2181378 の反応式
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:36])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(Cl)(C)(=O)=O.[OH-].[Na+]>C1COCC1.C(O)C.O>[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@H:23]1[OH:36])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 14798Sodium Hydroxide2 回HCID 31297Methanesulfonyl chlorideHCID 5141781-(2-Deoxy-5-O-(triphenylmethyl)pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 117550831-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 50-ml one-necked flask with lateral stopcock, 5′-O-tritylthymidine and triethylamine are placed in THF at t=0° C. under inert gas and stirring. Mesyl chloride is added dropwise from a syringe. The initially colorless solution becomes faintly yellow and cloudy. The reaction solution is allowed to warm up to room temperature within 30 minutes under stirring. Instead of the spot corresponding to starting material (Rf=0.29), a spot corresponding to the mesylated compound (Rf=0.45) is evident in TLC (V(MeOH):V(CH2Cl2)=1:19). At this point, 5 ml each of water, ethanol and 1 M sodium hydroxide solution are added to the reaction solution, which is stirred for 1 hour under reflux. In the TLC control test (V(MeOH):(VCH2Cl2)=1:19), exclusively the spot corresponding to the anhydro compound (Rf=0.15) is visible. Thereafter 3.4 ml of 10 M sodium hydroxide solution is added and the mixture stirred for 30 minutes under reflux. Two phases can form during this step. Instead of a spot corresponding to the anhydro compound (Rf=0.15), the product spot (Rf=0.33) is now evident on the TLC plate (V(MeOH):V(CH2Cl2)=1:19). The reaction solution is mixed with about 6 g of silica gel 60, and the solvent mixture is distilled off in the rotary evaporator. Subsequent column chromatography under flash conditions (silica gel 60; Ø=2.9 cm; h=32 cm; V(MeOH):V(CH2Cl2)=1:19+0.1% of triethylamine; 8.5 ml/min) yields the product, 1-(5-O-trityl-2-deoxy-β-D-lyxofuranosyl)thymine.

後処理

  1. stirringunder stirring
  2. stirringis stirred for 1 hour
  3. temperatureunder reflux
  4. stirringthe mixture stirred for 30 minutes
  5. temperatureunder reflux
  6. customTwo phases can form during this step
  7. additionThe reaction solution is mixed with about 6 g of silica gel 60
  8. distillationthe solvent mixture is distilled off in the rotary evaporator

出典と根拠

ORDレコード
ord-29f59da9b23543f2a9e7e07855e33004
出典データセット
uspto-grants-2005_05
特許番号
US06891033B2

反応ノート

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