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【结 构 式】 
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【药物名称】 【化学名称】(1-Naphthyl)methylphosphonic acid 4,5,6-trimethoxy-3-oxo-1,3-dihydrobenzofuran-1-yl diester 【CA登记号】 【 分 子 式 】C33H31O13P 【 分 子 量 】666.58102 |
【开发单位】Metabasis (Originator) 【药理作用】Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems |
合成路线1
Iodination of 3,4,5-trimethoxybenzyl alcohol (I) with iodine in the presence of silver trifluoroacetate gave the 2-iodobenzyl alcohol (II). Subsequent palladium-catalyzed carbonylation-lactonization reaction with (II) gave rise to phthalide (III). This was brominated using NBS to afford the 3-bromophthalide (IV). Finally, condensation of (IV) with (1-naphthyl)methylphosphonic acid (V) yielded the title bisphthalidyl phosphonate.
| 【1】 Dang, Q.; et al.; Synthesis of phosphonate 3-phthalidyl esters as prodrugs for potential intracellular delivery of phosphonates. Bioorg Med Chem Lett 1999, 9, 11, 1505. |
| 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) | 23613 | (3,4,5-trimethoxyphenyl)methanol | 3840-31-1 | C10H14O4 | 详情 | 详情 |
| (II) | 34420 | (2-iodo-3,4,5-trimethoxyphenyl)methanol | C10H13IO4 | 详情 | 详情 | |
| (III) | 34421 | 5,6,7-trimethoxy-2-benzofuran-1(3H)-one | C11H12O5 | 详情 | 详情 | |
| (IV) | 34422 | 3-bromo-5,6,7-trimethoxy-2-benzofuran-1(3H)-one | C11H11BrO5 | 详情 | 详情 | |
| (V) | 34423 | 1-naphthylmethylphosphonic acid | 4730-77-2 | C11H11O3P | 详情 | 详情 |
Extended Information