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【结 构 式】

【分子编号】16657

【品名】(4S,5S)-2-[(1S)-5-bromo-1-methylpentyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

【CA登记号】

【 分 子 式 】C20H36BBrO2

【 分 子 量 】399.21964

【元素组成】C 60.17% H 9.09% B 2.71% Br 20.02% O 8.02%

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:(XVI)

2) Other chiral directors, such as (S,S)-1,2-dicyclohexylethane-1,2-diol (XII), have also been used. Thus, the trans-esterification of boronate (IV) with diol (XII) gives the cyclic boronate (XIII), which was submitted to the previously described homologation with dichloromethane and butyllithium in THF to the intermediate (XIV). The treatment of (XIV) with anhydrous ZnCl2 as before yields the corresponding 5-bromo-1-chloroboronate (XV), which is methylated with methylmagnesium bromide as before affording the 5-bromo-1-methylboronate (XVI). The oxidative cleavage of (XVI) with Na2CO3 and H2O2 in THF affords 6-bromohexan-2(R)-ol (XVII), which is finally condensed with 3,7-dimethylxanthine (X) by means of NaH in DMSO.

1 Graul, J.; Casas, A.; Castañer, J.; Lisofylline. Drugs Fut 1997, 22, 5, 492.
2 Bianco, J.A.; Woodson, P.; Porubek, D.; Singer, J. (Cell Therapeutics, Inc.); Enantiomeric hydroxylated xanthine cpds. JP 1994509584; JP 1996259565; WO 9317684 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 16645 dimethyl 4-bromobutylboronate C6H14BBrO2 详情 详情
(X) 16651 theobromine; 3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione 83-67-0 C7H8N4O2 详情 详情
(XII) 16653 1,2-Dicyclohexyl-ethane-1,2-diol; 1,2-Dicyclohexyl-1,2-ethanediol 92319-61-4 C14H26O2 详情 详情
(XIII) 16654 (4S,5S)-2-(4-bromobutyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane C18H32BBrO2 详情 详情
(XIV) 16655     C19H33BBrCl2LiO2 详情 详情
(XV) 16656 (4S,5S)-2-[(1S)-5-bromo-1-chloropentyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane C19H33BBrClO2 详情 详情
(XVI) 16657 (4S,5S)-2-[(1S)-5-bromo-1-methylpentyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane C20H36BBrO2 详情 详情
(XVII) 16658 (2R)-6-bromo-2-hexanol C6H13BrO 详情 详情
Extended Information