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【结 构 式】 
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【药物名称】 【化学名称】[5S-(5alpha,6beta,11beta,12alpha)]-5-(Benzoyloxy)-4,6-dihydroxy-12-(2-hydroxyethoxy)-9,13,13-trimethyl-11-(phenylsulfanyl)-5,6,7,8,11,12-hexahydro-6,10-methanobenzocyclodecen-8-one 【CA登记号】 【 分 子 式 】C33H34O7S 【 分 子 量 】574.69873 |
【开发单位】Tokyo Institute of Technology (Originator), University of Tokyo (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS |
合成路线1
The reaction of the chiral hydroxyaldehyde (I) with the phenyllithium derivative (II) gives the condensation product (III), which is protected with methylboronic acid yielding the cyclic boronate (IV). The cyclization of (IV) by means of TiCl4 followed by a treatment with HF affords the tricyclic tetrol (V), which is finally selectively benzoylated with benzoic acid and DCC to give the target monobenzoate.
| 【1】 Morihira, K.; Nishimori, T.; Kusama, H.; Horiguchi, Y.; Kuwajima, I.; Tsuruo, T.; Synthesis of C-ring aromatic taxoids and evaluation of their multi-drug resistance reversing activity. Bioorg Med Chem Lett 1998, 8, 21, 2973. |
| 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) | 27204 | (1S)-1-hydroxy-4,6,6-trimethyl-5-[(E)-(phenylsulfanyl)methylidene]-3-[(triisopropylsilyl)oxy]-3-cyclohexene-1-carbaldehyde | C26H40O3SSi | 详情 | 详情 | |
| (II) | 27205 | [2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl]lithium | C11H13LiO4 | 详情 | 详情 | |
| (III) | 27206 | (1S)-1-[[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl](hydroxy)methyl]-4,6,6-trimethyl-5-[(E)-(phenylsulfanyl)methylidene]-3-[(triisopropylsilyl)oxy]-3-cyclohexen-1-ol | C37H54O7SSi | 详情 | 详情 | |
| (IV) | 27207 | (5S)-4-[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl]-2,8,10,10-tetramethyl-9-[(E)-(phenylsulfanyl)methylidene]-1,3-dioxa-2-boraspiro[4.5]dec-7-en-7-yl triisopropylsilyl ether | C38H55BO7SSi | 详情 | 详情 | |
| (V) | 27208 | (1S,2S,9R,10R)-1,2,4-trihydroxy-9-(2-hydroxyethoxy)-12,15,15-trimethyl-10-(phenylsulfanyl)tricyclo[9.3.1.0(3,8)]pentadeca-3,5,7,11-tetraen-13-one | C26H30O6S | 详情 | 详情 | |
| (VI) | 27209 | 2-nitroacetamide | C2H4N2O3 | 详情 | 详情 | |
| (VII) | 10202 | Benzoic acid | 65-85-0 | C7H6O2 | 详情 | 详情 |