(4S,5S)-2-(4-bromobutyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane -Drug Synthesis Database

【结构式】

【分子编号】16654

【品名】(4S,5S)-2-(4-bromobutyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

【CA登记号】

【分子式】C₁₈H₃₂BBrO₂

【分子量】371.16588

【元素组成】C 58.25% H 8.69% B 2.91% Br 21.53% O 8.62%

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：(XIII)

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.

参考文献中间体

合成目标

【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