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【结 构 式】

【分子编号】16697

【品名】diethyl (4S,5S)-2-isopropyl-1,3-dioxolane-4,5-dicarboxylate

【CA登记号】

【 分 子 式 】C12H20O6

【 分 子 量 】260.2872

【元素组成】C 55.37% H 7.74% O 36.88%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

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).

1 Kim, Y.; Rim, J.; Yoo, K.; Kim, G.; Gam, J.; Kim, K.H.; Kim, D.-K.; Song, S.; Synthesis of carbon-14 labelled cis-malonato[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane] platinum(II) (SKI 2053R). J Label Compd Radiopharm 1994, 34, 2, 157-64.
2 Kim, D.-K.; Kim, K.H.; SKI-2053R. Drugs Fut 1995, 20, 11, 1128.
3 Kim, D.-K.; Cho, Y.-B.; Park, J.-G.; Tai, J.-H.; Kim, K.H.; Hong, W.-S.; Kim, H.-T.; Kim, G.; Gam, J.; Synthesis and antitumor activity of a series of [2-substituted-4,5-bis(aminomethyl)-1,3-dioxolane]platinum(II) complexes. J Med Chem 1994, 37, 10, 1471-85.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 16695 (2S,3S)-2,3-dihydroxybutanedioic acid; D-(-)-Tartaric Acid; D-Tartaric Acid; (2S,3S)-2,3-dihydroxysuccinic acid 147-71-7 C4H6O6 详情 详情
(II) 16696 Diethyl L-(+)-Tartrate; diethyl (2S,3S)-2,3-dihydroxybutanedioate 87-91-2 C8H14O6 详情 详情
(III) 16697 diethyl (4S,5S)-2-isopropyl-1,3-dioxolane-4,5-dicarboxylate C12H20O6 详情 详情
(IV) 16698 [(4R,5R)-5-(hydroxymethyl)-2-isopropyl-1,3-dioxolan-4-yl]methanol C8H16O4 详情 详情
(V) 16699 (4R,5R)-2-isopropyl-4,5-bis([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1,3-dioxolane C14H28O4S2 详情 详情
(VI) 16700 1-[[(4R,5R)-2-isopropyl-5-(triazanylmethyl)-1,3-dioxolan-4-yl]methyl]triazane C8H22N6O2 详情 详情
(VII) 16701 [(4R,5R)-5-(aminomethyl)-2-isopropyl-1,3-dioxolan-4-yl]methylamine; [(4R,5R)-5-(aminomethyl)-2-isopropyl-1,3-dioxolan-4-yl]methanamine C8H18N2O2 详情 详情
(VIII) 16702 cis-diiodo[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]platinum; cis-[(4R,5R)-2-isopropyl-1,3-dioxolane-4,5-dimethanamine-N,N']diiodoplatinum C8H16I2N2O2Pt 详情 详情
(IX) 16703 malonic acid disilver salt C3H2Ag2O4 详情 详情
Extended Information