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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (5S)-((3R,3aR,6R,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)-hexahydrofuro[3,2-b]furan-3-yl)5,6-bis(nitrooxy)hexanoate

HRID 1675999
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HRID 1675999 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[C@H:12]2[O:13][CH2:14][C@@H:15]([OH:16])[C@H:11]2[O:10][CH2:9]1.[N+:17]([O:20][C@H:21]([CH2:28][O:29][N+:30]([O-:32])=[O:31])[CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])([O-:19])=[O:18].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N+:17]([O:20][C@H:21]([CH2:28][O:29][N+:30]([O-:32])=[O:31])[CH2:22][CH2:23][CH2:24][C:25]([O:16][C@@H:15]1[CH2:14][O:13][C@@H:12]2[C@H:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH2:9][O:10][C@H:11]12)=[O:26])([O-:19])=[O:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 29923588(S)-5,6-di(nitrooxy)hexanoic acidHCID 58209383(3R,3aR,6R,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

생성물 1

HCID 58209457(5S)-((3R,3aR,6R,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)-hexahydrofuro[3,2-b]furan-3-yl)5,6-bis(nitrooxy)hexanoate

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (3R,3aR,6R,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (2.96 g, 12.9 mmol) in DCM (40.8 mL) a solution of the crude (S)-5,6-di(nitrooxy)hexanoic acid (3.06 g, 12.85 mmol) (Step D) in DCM (9.15 mL) was added followed by EDAC (3.69 g, 19.28 mmol) and 4-dimethylaminopyridine (175 mg, 1.28 mmol). The reaction mixture was stirred at rt for 16.5 hrs. The solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 10 to 60%), affording the title product as pale yellow oil.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe crude residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 10 to 60%)

출처 및 근거

ORD 기록
ord-98acf9c32d9e4dc4afd688bb205becce
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08003811B2

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