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【结 构 式】 
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【分子编号】44152 【品名】methyl 3,4,5-tris(acetoxy)-6-(4-formylphenoxy)tetrahydro-2H-pyran-2-carboxylate 【CA登记号】 |
【 分 子 式 】C20H22O11 【 分 子 量 】438.38808 【元素组成】C 54.8% H 5.06% O 40.15% |
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：(XII)Intermediate (VIII) can be obtained as follows: Bromination of glucuronate derivative (X) by means of TiBr4 in CH2Cl2 followed by reaction with p-hydroxybenzaldehyde (XI) in acetonitrile in the presence of Ag2O affords derivative (XII), whose aldehyde moiety is then reduced by means of NaBH4 and silica gel in isopropanol/CHCl3 to provide benzyl alcohol (XIII). Finally, O-acetyl groups of (XIII) are cleaved by means of NaOMe in MeOH to furnish intermediate (VIII).
| 【1】 Leu, Y.-L.; Roffler, S.R.; Chern, J.-W.; Design and synthesis of water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT). J Med Chem 1999, 42, 18, 3623. |
| 【2】 Chern, J.-W.; Roffler, S.; Leu, Y.-L. (Academia Sinica); Proactive antitumor cpds.. EP 0990661; US 6043367 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 44150 | methyl 3,4,5-trihydroxy-6-[4-(hydroxymethyl)phenoxy]tetrahydro-2H-pyran-2-carboxylate | C14H18O8 | 详情 | 详情 | |
| (X) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (XI) | 44154 | methyl 3,4,5,6-tetrakis(acetoxy)tetrahydro-2H-pyran-2-carboxylate | C15H20O11 | 详情 | 详情 | |
| (XII) | 44152 | methyl 3,4,5-tris(acetoxy)-6-(4-formylphenoxy)tetrahydro-2H-pyran-2-carboxylate | C20H22O11 | 详情 | 详情 | |
| (XIII) | 44153 | methyl 3,4,5-tris(acetoxy)-6-[4-(hydroxymethyl)phenoxy]tetrahydro-2H-pyran-2-carboxylate | C20H24O11 | 详情 | 详情 |
Extended Information