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【结 构 式】 
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【分子编号】40582 【品名】 【CA登记号】 |
【 分 子 式 】C79H89Cl2N7O21Si 【 分 子 量 】1571.60114 【元素组成】C 60.38% H 5.71% Cl 4.51% N 6.24% O 21.38% Si 1.79% |
合成路线1
该中间体在本合成路线中的序号：(XXXI)The cyclization of (XXX) by means of PyBop gives the complete teicoplanin ring assembly (XXXI), which is deprotected at the Mom-O-CH2 group with Br-catecholborane yielding the primary alcohol (XXXII), which is oxidized with Dess Martin periodinane (DMP) and NaClO2 to afford the corresponding carboxylic acid (XXXIII). Finally, (XXXIII) is fully deprotected with AlBr3/Et-S affording the target teicoplanin aglucon.
| 【1】 Boger, D.L.; et al.; First and second generation total synthesis of the teicoplanin aglycon. J Am Chem Soc 2001, 123, 9, 1862. |
| 【2】 Boger, D.L.; et al.; Total synthesis of the teicoplanin aglycon. J Am Chem Soc 2000, 122, 30, 7416. |
合成路线2
该中间体在本合成路线中的序号：(XXVII)The reaction of the amino group of (XXV) with tBu-ONO, BHF4 and CuCl/CuCl2 gives the expected chloro derivative (XXVI), which is silylated at the OH group with CF3CON(Me)-Tbdms, yielding the silyl ether (XXVII). Elimination of the Mem protecting group of (XXVII) with the bromoboronate (XXVIII) affords the carbinol (XXIX), which is oxidized with DMP and NaClO2 to the corresponding carboxylic acid (XXX).
| 【1】 Boger, D.L.; et al.; First and second generation total synthesis of the teicoplanin aglycon. J Am Chem Soc 2001, 123, 9, 1862. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXV) | 47049 | tert-butyl (1S,2R,19R,22R,34S,37R,40R,52S)-15-amino-5-chloro-2-hydroxy-26,31,44,47,49,66-hexamethoxy-52-(((2-methoxyethoxy)methoxy)methyl)-21,35,38,54,56,58-hexaoxo-7,13,28-trioxa-20,36,39,53,55,57-hexaazaundecacyclo[38.14.2.2(3,6).2(14,17).2(19,34).1(8,12).1(23,27).1(29,33).1(41,45).0(10,37).0(46,51)]hexahexaconta-3,5,8(66),9,11,14,16,23(65),24,26,29(carbamate | C73H77ClN8O21 | 详情 | 详情 | |
| (XXVI) | 47050 | tert-butyl (1S,2R,19R,22R,34S,37R,40R,52S)-5,15-dichloro-2-hydroxy-26,31,44,47,49,66-hexamethoxy-52-(((2-methoxyethoxy)methoxy)methyl)-21,35,38,54,56,58-hexaoxo-7,13,28-trioxa-20,36,39,53,55,57-hexaazaundecacyclo[38.14.2.2(3,6).2(14,17).2(19,34).1(8,12).1(23,27).1(29,33).1(41,45).0(10,37).0(46,51)]hexahexaconta-3,5,8(66),9,11,14,16,23(65),24,26,29(carbamate | C73H75Cl2N7O21 | 详情 | 详情 | |
| (XXVII) | 40582 | C79H89Cl2N7O21Si | 详情 | 详情 | ||
| (XXVIII) | 42057 | 2-Bromo-1,3,2-benzodioxaborole; B-Bromocatecholborane | 51901-85-0 | C6H4BBrO2 | 详情 | 详情 |
| (XXIX) | 40583 | C75H81Cl2N7O19Si | 详情 | 详情 | ||
| (XXX) | 40584 | C75H79Cl2N7O20Si | 详情 | 详情 |