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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 2 条

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.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXX) 40581   C79H91Cl2N7O22Si 详情 详情
(XXXI) 40582   C79H89Cl2N7O21Si 详情 详情
(XXXII) 40583   C75H81Cl2N7O19Si 详情 详情
(XXXIII) 40584   C75H79Cl2N7O20Si 详情 详情

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
Extended Information