• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】48786

【品名】2-[2-methoxy-3-(methoxycarbonyl)-6-methyl-4-pyridinyl]acetic acid

【CA登记号】

【 分 子 式 】C11H13NO5

【 分 子 量 】239.22796

【元素组成】C 55.23% H 5.48% N 5.85% O 33.44%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

The intermediate propionic aldehyde (VI) has been obtained by two different ways: 1. The cyclization of 2-methoxy-4,6-dimethylpyridine-3-carboxylic acid methyl ester (I) with the cyclohexenone derivative (II) by means of LDA, followed by aromatization with DDQ gives the tricyclic ketone (III), which is methylated with Me-I and K2CO3 to yield the dimethoxyketone (IV). The desilylation of (IV) with TBAF affords the propanol derivative (V), which is finally submitted to a Swern oxidation to provide the desired intermediate, the propionic aldehyde (VI). 2. The reaction of pyridine-3-carboxylate (I) with LDA and CO2 gives the dicarboxylic hemiester (VII), which is hydrolyzed with KOH and anhydrized to yield the homophthalic anhydride (VIII). The cyclization of (VIII) with the alpha-sulfinylcyclohexenone (IX) by means of NaH affords the tricyclic ketone (X), which is methylated with Me-I and K2CO3 to provide the dimethoxyketone (XI). Finally, the ethyleneketal group of (XI) is hydrolyzed with TFA to furnish the desired intermediate, the propionic aldehyde (VI). The cyclization of (VI) by means of SmI2 gives the tetracyclic diol (XII), which is submitted to a Swern oxidation to yield the alpha-hydroxyketone (XIII). The dehydration of (XIII) by means of the Burgess reagent yields the cyclohexenone derivative (XIV), which is finally asymmetrically reduced to the (R)-alcohol (XV) by means of BH3 using a chiral borane as catalyst.

1 Kita, Y.; et al.; Enantioselective total synthesis of a potent antitumor antibiotic, fredericamycin A. J Am Chem Soc 2001, 123, 14, 3214.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
48787 (2-ethoxyethynyl)(trimethyl)silane; ethyl 2-(trimethylsilyl)ethynyl ether C7H14OSi 详情 详情
(I) 48780 methyl 2-methoxy-4,6-dimethylnicotinate C10H13NO3 详情 详情
(II) 48781 6-(3-[[tert-butyl(dimethyl)silyl]oxy]propyl)-2-cyclohexen-1-one C15H28O2Si 详情 详情
(III) 48782 8-(3-[[tert-butyl(dimethyl)silyl]oxy]propyl)-10-hydroxy-1-methoxy-3-methyl-7,8-dihydrobenzo[g]isoquinolin-9(6H)-one C24H35NO4Si 详情 详情
(IV) 48783 8-(3-[[tert-butyl(dimethyl)silyl]oxy]propyl)-1,10-dimethoxy-3-methyl-7,8-dihydrobenzo[g]isoquinolin-9(6H)-one C25H37NO4Si 详情 详情
(V) 48784 8-(3-hydroxypropyl)-1,10-dimethoxy-3-methyl-7,8-dihydrobenzo[g]isoquinolin-9(6H)-one C19H23NO4 详情 详情
(VI) 48785 3-(1,10-dimethoxy-3-methyl-9-oxo-6,7,8,9-tetrahydrobenzo[g]isoquinolin-8-yl)propanal C19H21NO4 详情 详情
(VII) 48786 2-[2-methoxy-3-(methoxycarbonyl)-6-methyl-4-pyridinyl]acetic acid C11H13NO5 详情 详情
(VIII) 48788 8-methoxy-6-methyl-1H-pyrano[3,4-c]pyridine-1,3(4H)-dione C10H9NO4 详情 详情
(IX) 48789 6-[2-(1,3-dioxolan-2-yl)ethyl]-2-(phenylsulfinyl)-2-cyclohexen-1-one C17H20O4S 详情 详情
(X) 48790 8-[2-(1,3-dioxolan-2-yl)ethyl]-10-hydroxy-1-methoxy-3-methyl-7,8-dihydrobenzo[g]isoquinolin-9(6H)-one C20H23NO5 详情 详情
(XI) 48793 8-[2-(1,3-dioxolan-2-yl)ethyl]-1,10-dimethoxy-3-methyl-7,8-dihydrobenzo[g]isoquinolin-9(6H)-one C21H25NO5 详情 详情
(XII) 48791 10,11-dimethoxy-8-methyl-1,2,3,3a,4,5-hexahydro-11bH-indeno[5,4-g]isoquinoline-1,11b-diol C19H23NO4 详情 详情
(XIII) 48792 11b-hydroxy-10,11-dimethoxy-8-methyl-2,3,3a,4,5,11b-hexahydro-1H-indeno[5,4-g]isoquinolin-1-one C19H21NO4 详情 详情
(XIV) 48738 10,11-dimethoxy-8-methyl-2,3,4,5-tetrahydro-1H-indeno[5,4-g]isoquinolin-1-one C19H19NO3 详情 详情
(XV) 48739 (1R)-10,11-dimethoxy-8-methyl-2,3,4,5-tetrahydro-1H-indeno[5,4-g]isoquinolin-1-ol C19H21NO3 详情 详情
Extended Information