4-Toluenesulfonyl chloride → [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate

HRID 60695노트

반응식

HRID 60695 반응식
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([C@H:10]([OH:13])[CH2:11][OH:12])[CH2:9][C@H:4]2[O:3]1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:12][CH2:11][C@H:10]([C@H:8]2[O:7][C@@H:5]3[O:6][C:2]([CH3:14])([CH3:1])[O:3][C@@H:4]3[CH2:9]2)[OH:13])(=[O:23])=[O:22])=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 11084935(R)-1-((3AR,5S,6AR)-2,2-Dimethyltetrahydrofuro[2,3-D][1,3]dioxol-5-YL)ethane-1,2-diol

생성물 1

HCID 15473566[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate수율 74%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (100 g, 490 mmol) in dry pyridine (1000 mL) was added p-toluenesulfonyl chloride (139 g, 735 mmol) at 0° C. After being stirred at room temperature for 12 hours, the resulted solution was quenched by water (100 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:10 to 1:3 EtOAc in petroleum ether) to afford 130 g of [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate (compound 6a) as a slight yellow oil.

후처리

  1. customthe resulted solution was quenched by water (100 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:10 to 1:3 EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-6f26cc8ea12e4ece879f4c629c42d544
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

반응 노트

불러오는 중…