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

反応式

HRID 64246 の反応式
[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

参加物

4

反応物 2

HCID 60750GemcitabineHCID 1724041,3-Dichlorotetraisopropyldisiloxane

生成物 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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-391119ebd8214ccba3a41b7a857c9475
出典データセット
uspto-grants-2016_09
特許番号
US09447137B2

関連ノート

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