Methanol → Methyl 2-deoxy-5-O-(triphenylmethyl)-D-erythro-pentofuranoside

HRID 1199117노트

반응식

HRID 1199117 반응식
[O:1]([CH3:10])[CH:2]1[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[CH2:3]1.[C:11]1([C:17](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO>N1C=CC=CC=1>[C:17]([O:9][CH2:8][C@H:6]1[O:7][CH:2]([O:1][CH3:10])[CH2:3][C@@H:4]1[OH:5])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 6456Trityl chlorideHCID 10154128Methyl 2-deoxy-D-erythro-pentofuranoside

생성물 1

HCID 13912247Methyl 2-deoxy-5-O-(triphenylmethyl)-D-erythro-pentofuranoside

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 11.2 g (0.07 mole) of methyl 2-deoxyribofuranoside (90% pure) in 60 ml of dry pyridine under a dry nitrogen atmosphere were added 19.0 g (0.07 mole) of triphenylmethyl chloride. The mixture was stirred at ambient temperature for three days. Methanol (35 ml) was then added. The solvents were then evaporated under reduced pressure. The residue was taken up in 200 ml of ethyl acetate, washed with 75 ml of 5% sodium bicarbonate followed by a 75 ml wash with DI (deionized) water. The organic layer was dried (Na2SO4), filtered and the solvent removed under vacuum affording a sticky, viscous oil. This crude methyl 2-deoxy-5-O-tritylriboruanoside compound was used without further purification in subsequent synthetic procedures.

후처리

  1. customThe solvents were then evaporated under reduced pressure
  2. washwashed with 75 ml of 5% sodium bicarbonate
  3. washwash with DI (deionized) water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customaffording a sticky, viscous oil
  8. customThis crude methyl 2-deoxy-5-O-tritylriboruanoside compound was used without further purification in subsequent synthetic procedures

출처 및 근거

ORD 기록
ord-ceaee069a7f34363861c0da5be98141e
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04898936

반응 노트

불러오는 중…