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【结 构 式】

【分子编号】25622

【品名】4-(3-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-2,5-dimethoxy[1,1'-biphenyl]-3,4'-diol

【CA登记号】

【 分 子 式 】C22H20O7

【 分 子 量 】396.3966

【元素组成】C 66.66% H 5.09% O 28.25%

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:(XXI)

2. In an alternative synthesis, 5-bromosalicylaldehyde (XIII) was alkylated with bromoacetaldehyde dimethyl acetal (XIV) to afford ether (XV). Further Baeyer-Villiger reaction with (XV) produced phenol (XVI), which was cyclized to the benzodioxine (XVII) with p-TsOH. Lithiation of (XVII), followed by reaction with triisopropyl borate and hydrolytic work-up, gave boronic acid (XVIII). Aldehyde (II) was treated with MCPBA yielding phenol (XIII), which was iodinated in the presence of tert-butylamine to give the bromo iodo derivative (XIV). Sequential Suzuki coupling of bromo iodo compound (XIV) with boronic acid (XVIII) yielding (XIX), and then with boronic acid (I) provided terphenyl (XX). Hydrolysis of the methyl acetal of (XX) using p-TsOH gave cyclic hemiacetal (XXI). Finally, Wittig reaction of (XXI) with the phosphorane prepared from isopropyl triphenylphosphonium iodide and n-BuLi provided the title compound.

1 Yonezawa, S.; et al.; Total synthesis of terprenin, a novel immunosuppressive p-terphenyl derivative. J Org Chem 1998, 63, 17, 5831.
2 Nagashima, K.; Kamigauchi, T.; Sakazaki, R.; et al.; Terprenins, novel immunosuppressants produced by Aspergillus candidus. J Antibiot 1998, 51, 4, 445.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIIIa) 25618 3-bromo-2,5-dimethoxyphenol C8H9BrO3 详情 详情
(XIVb) 25619 3-bromo-6-iodo-2,5-dimethoxyphenol C8H8BrIO3 详情 详情
(I) 25602 4-[[tert-butyl(dimethyl)silyl]oxy]phenylboronic acid C12H21BO3Si 详情 详情
(II) 25603 3-bromo-2,5-dimethoxybenzaldehyde C9H9BrO3 详情 详情
(XIII) 25613 5-bromo-2-hydroxybenzaldehyde; 5-Bromosalicylaldehyde 1761-61-1 C7H5BrO2 详情 详情
(XIV) 13183 2-Bromo-1,1-dimethoxyethane; 2-Bromo-1-methoxyethyl methyl ether; Bromoacetaldehyde dimethyl acetal 7252-83-7 C4H9BrO2 详情 详情
(XV) 25614 5-bromo-2-(2,2-dimethoxyethoxy)benzaldehyde C11H13BrO4 详情 详情
(XVI) 25615 5-bromo-2-(2,2-dimethoxyethoxy)phenol C10H13BrO4 详情 详情
(XVII) 25616 7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl methyl ether C9H9BrO3 详情 详情
(XVIII) 25617 3-methoxy-2,3-dihydro-1,4-benzodioxin-6-ylboronic acid C9H11BO5 详情 详情
(XIX) 25620 3-bromo-2,5-dimethoxy-6-(3-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl)phenol C17H17BrO6 详情 详情
(XX) 25621 2,5-dimethoxy-4-(3-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl)[1,1'-biphenyl]-3,4'-diol C23H22O7 详情 详情
(XXI) 25622 4-(3-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-2,5-dimethoxy[1,1'-biphenyl]-3,4'-diol C22H20O7 详情 详情
Extended Information