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【结 构 式】

【分子编号】25605

【品名】3'-formyl-2',5'-dimethoxy[1,1'-biphenyl]-4-yl methanesulfonate

【CA登记号】

【 分 子 式 】C16H16O6S

【 分 子 量 】336.36544

【元素组成】C 57.13% H 4.79% O 28.54% S 9.53%

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:(IV)

1. The Suzuki coupling of arylboronic acid (I) with 3-bromo-2,5-dimethoxybenzaldehyde (II) with concomitant desilylation provided biphenyl aldehyde (III). After protection of the phenolic hydroxyl as the mesylate (IV), selective bromination of (IV) in the presence of NaOAc in AcOH provided bromoaldehyde (V). A Baeyer-Villiger oxidation of the aldehyde group of (V) with m-chloroperbenzoic acid, followed by acid hydrolysis of the intermediate formate ester, produced phenol (VI). which was coupled with protected boronic acid (VII) in the presence of Pd(PPh3)4 to yield terphenyl (VIII). Mesylation of the hydroxyl groups of (VIII) and further hydrogenolytic cleavage of the benzyl ether gave phenol (X). Then, alkylationof (X) with prenyl bromide (XI) provided prenyl ether (XII). The mesylate groups of (XII) were finally removed by hydrolysis with KOH to furnish 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
(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
(III) 25604 4'-hydroxy-2,5-dimethoxy[1,1'-biphenyl]-3-carbaldehyde C15H14O4 详情 详情
(IV) 25605 3'-formyl-2',5'-dimethoxy[1,1'-biphenyl]-4-yl methanesulfonate C16H16O6S 详情 详情
(V) 25606 4'-bromo-3'-formyl-2',5'-dimethoxy[1,1'-biphenyl]-4-yl methanesulfonate C16H15BrO6S 详情 详情
(VI) 25607 4'-bromo-3'-hydroxy-2',5'-dimethoxy[1,1'-biphenyl]-4-yl methanesulfonate C15H15BrO6S 详情 详情
(VII) 25608 4-(benzyloxy)-3-[[tert-butyl(dimethyl)silyl]oxy]phenylboronic acid C19H27BO4Si 详情 详情
(VIII) 25609 Methanesulfonic acid 4''-benzyloxy-3',3''-dihydroxy-2',5'-dimethoxy-p-terphenyl-4-yl ester C28H26O8S 详情 详情
(IX) 25610 4-Benzyloxy-3',6'-dimethoxy-p-terphenyl-3,2',4''-triol tris methanesuolfonyl ester C30H30O12S3 详情 详情
(X) 25611 3',6'-Dimethoxy-p-terphenyl-2',3,4,4''-tetrol 2'-O,3-O,4''-O-tris methanesulfonate C23H24O12S3 详情 详情
(XII) 25612 3',6'-Dimethoxy-4-(3-methyl-2-butenyloxy)-p-terphenyl-2',3,4''-triol tris methanesulfonate C28H32O12S3 详情 详情
Extended Information