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【结 构 式】

【分子编号】28789

【品名】(1Z,3Z)-1-(1,3-butadiynyl)-4-[[2-(trimethylsilyl)ethyl]sulfanyl]-1,3-heptadien-5-ynyl 2-(trimethylsilyl)ethyl sulfide

【CA登记号】

【 分 子 式 】C21H32S2Si2

【 分 子 量 】404.78808

【元素组成】C 62.31% H 7.97% S 15.84% Si 13.88%

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:(X)

The addition of 2-(trimethylsilyl)ethylmercaptane (I) to 2,4-hexadiyn-1,6-diol (II) catalyzed by KOH in DMF gives the addition product (III), which is oxidized with Dess-Martin periodinane in dichloromethane or oxalyl chloride in DMSO yielding the dialdehyde (IV). The condensation of (IV) with tetrabromomethane by means of triphenylphosphine in dichloromethane affords the tetrabromo derivative (V), which is treated with butyllithium in THF to give the diacetylenic dianion (VI). The reaction of (V) with methyl iodide yields the methylated monoanion (VII), which is condensed with DMF catalyzed by boron trifluoride ethearate to afford the diacetylenic aldehyde (VIII). The reaction of (VIII) with tetrabromomethane/triphenylphosphine as before gives the dibromovinyl derivative (IX), which is treated with butyllithium as before yielding the triacetylenic compound (X). The condensation of (X) with vinyl bromide (XI) by means of Pd(PPh3)4/CuI/triethylamine in toluene affords the intermediate (XII), which is finally submitted to an oxidative cyclization by means of tetrabutylammonium fluoride and iodine.

1 Yang, W.; Koreeda, M.; Chemistry of 1,2-dithiins. Synthesis of the potent antibiotic thiarubrine A. J Am Chem Soc 1994, 116, 10793.
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) 28780 2,4-hexadiyne-1,6-diol 3031-68-3 C6H6O2 详情 详情
(II) 28781 2-(trimethylsilyl)-1-ethanethiol 18143-30-1 C5H14SSi 详情 详情
(III) 28782 (2Z,4Z)-2,5-bis[[2-(trimethylsilyl)ethyl]sulfanyl]-2,4-hexadiene-1,6-diol C16H34O2S2Si2 详情 详情
(IV) 28783 (2Z,4Z)-2,5-bis[[2-(trimethylsilyl)ethyl]sulfanyl]-2,4-hexadienedial C16H30O2S2Si2 详情 详情
(V) 28784 (1Z,3Z)-6,6-dibromo-1-(2,2-dibromovinyl)-4-[[2-(trimethylsilyl)ethyl]sulfanyl]-1,3,5-hexatrienyl 2-(trimethylsilyl)ethyl sulfide C18H30Br4S2Si2 详情 详情
(VI) 28785 3,6-Bis[2-(trimethylsilyl)ethylsulfanyl]octa-3,5-dien-1,7-diyne dilithium salt C18H28Li2S2Si2 详情 详情
(VII) 28786 ((3Z,5Z)-3,6-bis[[2-(trimethylsilyl)ethyl]sulfanyl]-3,5-nonadiene-1,7-diynyl)lithium C19H31LiS2Si2 详情 详情
(VIII) 28787 (4Z,6Z)-4,7-bis[[2-(trimethylsilyl)ethyl]sulfanyl]-4,6-decadiene-2,8-diynal C20H32OS2Si2 详情 详情
(IX) 28788 (1Z,3Z)-1-(4,4-dibromo-3-buten-1-ynyl)-4-[[2-(trimethylsilyl)ethyl]sulfanyl]-1,3-heptadien-5-ynyl 2-(trimethylsilyl)ethyl sulfide C21H32Br2S2Si2 详情 详情
(X) 28789 (1Z,3Z)-1-(1,3-butadiynyl)-4-[[2-(trimethylsilyl)ethyl]sulfanyl]-1,3-heptadien-5-ynyl 2-(trimethylsilyl)ethyl sulfide C21H32S2Si2 详情 详情
(XI) 28790 1-bromoethylene 593-60-2 C2H3Br 详情 详情
(XII) 28791 (1Z,3Z)-1-(5-hexene-1,3-diynyl)-4-[[2-(trimethylsilyl)ethyl]sulfanyl]-1,3-heptadien-5-ynyl 2-(trimethylsilyl)ethyl sulfide C23H34S2Si2 详情 详情
Extended Information