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【结 构 式】

【分子编号】48954

【品名】isobutyl trifluoromethanesulfonate

【CA登记号】

【 分 子 式 】C5H9F3O3S

【 分 子 量 】206.1858696

【元素组成】C 29.13% H 4.4% F 27.64% O 23.28% S 15.55%

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:(XXII)

Synthesis of the intermediate vinyl cuprate (XXV): The reaction of cyclohexyloxyacetylene (XXI) with iso-butyl triflate (XXII) by means of BuLi gives the adduct (XXIII), which is brominated with Tms-Br, yielding the vinyl bromide (XXIV). Finally, this compound is treated with CuCN, LiCl and tBuLi in THF to afford the desired vinyl cuprate intermediate (XXV).

1 Jin, Z.; Yu, W.; A new strategy for the stereoselective introduction of steroid side chain via alpha-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1. J Am Chem Soc 2001, 123, 14, 3369.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXI) 48953 1-(ethynyloxy)cyclohexane; cyclohexyl ethynyl ether C8H12O 详情 详情
(XXII) 48954 isobutyl trifluoromethanesulfonate C5H9F3O3S 详情 详情
(XXIII) 48955 1-[(4-methyl-1-pentynyl)oxy]cyclohexane; cyclohexyl 4-methyl-1-pentynyl ether C12H20O 详情 详情
(XXIV) 48956 (E)-1-bromo-4-methyl-1-pentenyl cyclohexyl ether; 1-[[(E)-1-bromo-4-methyl-1-pentenyl]oxy]cyclohexane C12H21BrO 详情 详情
(XXV) 48957   C54H99CuNO4 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XXII)

Alpha-(cyclohexloxy)vinyl bromide (XXIV): The reaction of (cyclohexyloxy)acetylene (XXI) with isobutyl triflate (XXII) by means of BuLi gives 1-(cyclohexyloxy)-4-methyl-1-pentyne (XXIII), which is then brominated to the target vinyl bromide (XXIV) by means of Tms-Br in methanol

1 Yu, W.; Jin, Z.; Total synthesis of the anticancer natural product OSW-1. J Am Chem Soc 2002, 124, 23, 6576.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXI) 48953 1-(ethynyloxy)cyclohexane; cyclohexyl ethynyl ether C8H12O 详情 详情
(XXII) 48954 isobutyl trifluoromethanesulfonate C5H9F3O3S 详情 详情
(XXIII) 48955 1-[(4-methyl-1-pentynyl)oxy]cyclohexane; cyclohexyl 4-methyl-1-pentynyl ether C12H20O 详情 详情
(XXIV) 48956 (E)-1-bromo-4-methyl-1-pentenyl cyclohexyl ether; 1-[[(E)-1-bromo-4-methyl-1-pentenyl]oxy]cyclohexane C12H21BrO 详情 详情
Extended Information