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【结 构 式】 
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【分子编号】63158 【品名】6-[(triphenylmethyl)sulfanyl]-1,3,3-hexanetricarboxylic acid 【CA登记号】 |
【 分 子 式 】C28H28O6S 【 分 子 量 】492.59272 【元素组成】C 68.27% H 5.73% O 19.49% S 6.51% |
合成路线1
该中间体在本合成路线中的序号：(VII)Acylation of Meldrum's acid (I) with 3-tryphenylmethylsulfanyl)propionic acid (II) by means of DCC produces the intermediate adduct (III), which is subsequently reduced to the tritylsulfanyl derivative (IV) by using NaBH4/AcOH. Alkylation of (IV) with methyl 3-bromopropionate (V) in the presence of NaOMe provides the 5,5-disubstituted dioxanedione (VI). Basic hydrolysis of (VI) gives rise to the tricarboxylic acid (VII), which is further decarboxylated to (VIII) in hot DMSO. Finally the S-trityl protecting gropu is removed by treatment with trifluoroacetic acid and triisopropylsilane.
| 【1】 Jackson, P.F.; Slusher, B.S.; Majer, P.; Maclin, K.M.; Wang, E.; Lapidus, R.S. (Guilford Pharmaceuticals Inc.); NAALADase inhibitors useful as pharmaceutical cpds. and compsns.. JP 2002519408; US 6395718; WO 0001668 . |
| 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) | 14738 | Meldrum's acid; 2,2-dimethyl-1,3-dioxane-4,6-dione；Malonic acid cyclic isopropylidene ester | 2033-24-1 | C6H8O4 | 详情 | 详情 |
| (II) | 63154 | 3-[(triphenylmethyl)sulfanyl]propanoic acid | C22H20O2S | 详情 | 详情 | |
| (III) | 63155 | 5-{1-hydroxy-3-[(triphenylmethyl)sulfanyl]propylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione | C28H26O5S | 详情 | 详情 | |
| (IV) | 63156 | 2,2-dimethyl-5-{3-[(triphenylmethyl)sulfanyl]propyl}-1,3-dioxane-4,6-dione | C28H28O4S | 详情 | 详情 | |
| (V) | 50285 | 3-Bromopropionic acid methyl ester; Methyl 3-bromopropionate | 3395-91-3 | C4H7BrO2 | 详情 | 详情 |
| (VI) | 63157 | methyl 3-(2,2-dimethyl-4,6-dioxo-5-{3-[(triphenylmethyl)sulfanyl]propyl}-1,3-dioxan-5-yl)propanoate | C32H34O6S | 详情 | 详情 | |
| (VII) | 63158 | 6-[(triphenylmethyl)sulfanyl]-1,3,3-hexanetricarboxylic acid | C28H28O6S | 详情 | 详情 | |
| (VIII) | 63159 | 2-{3-[(triphenylmethyl)sulfanyl]propyl}pentanedioic acid | C27H28O4S | 详情 | 详情 |