Eptaplatin, Heptaplatin, NSC-644591, NSC-D-644591, SKI-2053R, Sunpla
依铂(SKI-2053R)Chemical Name: cis-[(4R,5R)-2-Isopropyl-1,3-dioxolane-4,5-bis(methylamine)-N,N'][malonato(2-)-O,O']platinum; (SP-4-2)-[(4R,5R)-2-Isopropyl-1,3-dioxolane-4,5-bis(methanamine)-N,N'][propanedioato(2-)-O,O']platinum
CAS No. 146665-77-2
项目整合开发状态: Launched-1999
项目研究机构: SK Chemicals (Originator)
合成路线:Reaction of D-tartaric acid (I) with EtOH in the presence of an acid catalyst gives diethyl D-tartrate (II),which is treated with isobutyraldehyde and anhydrous CuSO4 in the presence of methanesulfonic acid yielding diethyl 2,3-O-isobutylidene-D-tartrate (III).The 1,3-dioxolane diester (III) was then reduced with LAH to afford (4R,5R)-4,5-bis(hydroxymethyl)-2-isopropyl-1,3-dioxolane (IV),which is treated with methanesulfonyl chloride in pyridine yielding (4R,5R)-4,5-bis(methylsulfonyloxymethyl)-2-isopropyl-1,3-dioxolane (V).The bis(methanesulfonate) (V) is reacted with NaN3 in DMF to give (4R,5R)-4,5-bis(azidomethyl)-2-isopropyl-1,3-dioxolane (VI),which is reduced with hydrogen in the presence of 10% Pd/C in EtOH to afford (4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane (VII).The diamine (VII) is reacted with an equimolar amount of in situ generated K2PtI4 to afford cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (VIII),which is finally treated with malonic acid disilver salt in H2O to obtain (IX).
📌 参考资料/链接：
参考文献标题:Synthesis and antitumor activity of a series of [2-substituted-4,5-bis(aminomethyl)-1,3-dioxolane]platinum(II) complexes
文献作者:Kim,D.-K.; Kim,G.; Gam,J.; Cho,Y.-B.; Kim,H.-T.; Tai,J.-H.; Kim,K.H.; Hong,W.-S.; Park,J.-G.
参考来源:J Med Chem 1994,37(10),1471-85
📄 详细内容
合成路线:Reaction of D-tartaric acid (I) with EtOH in the presence of an acid catalyst gives diethyl D-tartrate (II),which is treated with isobutyraldehyde and anhydrous CuSO4 in the presence of methanesulfonic acid yielding diethyl 2,3-O-isobutylidene-D-tartrate (III).The 1,3-dioxolane diester (III) was then reduced with LAH to afford (4R,5R)-4,5-bis(hydroxymethyl)-2-isopropyl-1,3-dioxolane (IV),which is treated with methanesulfonyl chloride in pyridine yielding (4R,5R)-4,5-bis(methylsulfonyloxymethyl)-2-isopropyl-1,3-dioxolane (V).The bis(methanesulfonate) (V) is reacted with NaN3 in DMF to give (4R,5R)-4,5-bis(azidomethyl)-2-isopropyl-1,3-dioxolane (VI),which is reduced with hydrogen in the presence of 10% Pd/C in EtOH to afford (4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane (VII).The diamine (VII) is reacted with an equimolar amount of in situ generated K2PtI4 to afford cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (VIII),which is finally treated with malonic acid disilver salt in H2O to obtain (IX).
参考文献标题:SKI-2053R
文献作者:Kim,D.-K.; Kim,K.H.
参考来源:Drugs Fut 1995,20(11),1128
合成路线:Reaction of D-tartaric acid (I) with EtOH in the presence of an acid catalyst gives diethyl D-tartrate (II),which is treated with isobutyraldehyde and anhydrous CuSO4 in the presence of methanesulfonic acid yielding diethyl 2,3-O-isobutylidene-D-tartrate (III).The 1,3-dioxolane diester (III) was then reduced with LAH to afford (4R,5R)-4,5-bis(hydroxymethyl)-2-isopropyl-1,3-dioxolane (IV),which is treated with methanesulfonyl chloride in pyridine yielding (4R,5R)-4,5-bis(methylsulfonyloxymethyl)-2-isopropyl-1,3-dioxolane (V).The bis(methanesulfonate) (V) is reacted with NaN3 in DMF to give (4R,5R)-4,5-bis(azidomethyl)-2-isopropyl-1,3-dioxolane (VI),which is reduced with hydrogen in the presence of 10% Pd/C in EtOH to afford (4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane (VII).The diamine (VII) is reacted with an equimolar amount of in situ generated K2PtI4 to afford cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (VIII),which is finally treated with malonic acid disilver salt in H2O to obtain (IX).
参考文献标题:Synthesis of carbon-14 labelled cis-malonato[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (SKI 2053R)
文献作者:Kim,Y.; Rim,J.; Yoo,K.; Kim,G.; Gam,J.; Kim,K.H.; Kim,D.-K.; Song,S.
参考来源:J Label Compd Radiopharm 1994,34(2),157-64
产品链接: CAS No. 146665-77-2››