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

HRID 2181378노트

반응식

HRID 2181378 반응식
[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

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 14798Sodium Hydroxide2회HCID 31297Methanesulfonyl chlorideHCID 5141781-(2-Deoxy-5-O-(triphenylmethyl)pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29f59da9b23543f2a9e7e07855e33004
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06891033B2

반응 노트

불러오는 중…