|
【结 构 式】 
|
【分子编号】48422 【品名】 【CA登记号】 |
【 分 子 式 】C69H128N2O14Si5 【 分 子 量 】1350.2079 【元素组成】C 61.38% H 9.56% N 2.07% O 16.59% Si 10.4% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The next steps for conversion of (XII) into (XIII) are: Dess-Martin oxidation, removal of the (p-methoxyphenyl)methyl group (MPM) by means of DDQ in phosphate buffer/tert-BuOH/CH2Cl2, hydrolysis of the methyl ester with LiOH in H2O/THF and, finally, Yamaguchi lactonization. Finally, the target product is obtained by removal of the TBDMS groups of lactone enone (XIII) with tetrabutyl ammonium fluoride (TBAF) in THF to furnish alcohol (XIV), followed by treatment with p-TsOH.Py (PPTS) in CH2Cl2, activation with p-nitrobenzoyl chloride in CH2Cl2 in the presence of pyridine, reaction with TBSOTf and Et3N in CH2Cl2, and final saponification with K2CO3 in MeOH.
| 【1】 Aicher, T.D.; et al.; Total synthesis of halichondrin B and norhalichondrin B. J Am Chem Soc 1992, 114, 8, 3162. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 48421 | C79H141NO16Si5 | 详情 | 详情 | ||
| (XIII) | 48422 | C69H128N2O14Si5 | 详情 | 详情 | ||
| (XIV) | 48423 | (3S,5S,7R,8R,10S,11S,12R,16R,19S,20R,21R,22S,23S,24S,30S,33S,36R,38R)-7,21,22,24-tetrahydroxy-8-(hydroxymethyl)-11,38-dimethyl-32,39-dimethylene-4,9,13,40,41,42,43-heptaoxa-1,26-diazaheptacyclo[34.3.1.1(16,20).1(19,23).1(30,33).0(3,12).0(5,10)]tritetracont-25-ene-14,27- | C39H58N2O14 | 详情 | 详情 |