Gemcitabine → 4-amino-1-((6aR,8R,9aR)-9,9-difluoro-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidin-2(1H)-one

HRID 64246

반응식

HRID 64246 반응식
[CH:1]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[N:3]([C@@H:9]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C:10]2([F:18])[F:17])[CH:2]=1.Cl[Si:20]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[O:21][Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24]>N1C=CC=CC=1>[NH2:8][C:7]1[CH:1]=[CH:2][N:3]([C@@H:9]2[O:13][C@H:12]3[C@@H:11]([O:16][Si:20]([CH:30]([CH3:32])[CH3:31])([CH:33]([CH3:35])[CH3:34])[O:21][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:24])[CH3:25])[O:15][CH2:14]3)[C:10]2([F:17])[F:18])[C:4](=[O:5])[N:6]=1

참가 물질

4

반응물 2

HCID 60750GemcitabineHCID 1724041,3-Dichlorotetraisopropyldisiloxane

생성물 1

HCID 901365764-amino-1-((6aR,8R,9aR)-9,9-difluoro-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidin-2(1H)-one

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

As shown above, Gemcitabine (4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one) can be treated with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (TIPDSiCl2) in dry pyridine to provide 4-amino-1-((6aR,8R,9aR)-9,9-difluoro-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidin-2(1H)-one. It is contemplated that other 1,3-dihalo-1,1,3,3-tetraalkyldisiloxanes can be used in place of TIPDSiCl2. It is also contemplated that two monofunctional halosiloxane protecting groups can be used in place of the difunctional TIPDSiCl2. Further, it is also contemplated that other hydroxyl protecting groups (e.g., tetrahydropyranyl (THP) or acetyl (Ac)) can be used in place of TIPDSiCl2.

출처 및 근거

ORD 기록
ord-391119ebd8214ccba3a41b7a857c9475
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447137B2

연결된 노트

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