(1R,2S,6R,8R)-4-[(1S)-4-bromo-1-chlorobutyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane -Drug Synthesis Database

【结构式】

【分子编号】35560

【品名】(1R,2S,6R,8R)-4-[(1S)-4-bromo-1-chlorobutyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane

【CA登记号】

【分子式】C₁₄H₂₃BBrClO₂

【分子量】349.50312

【元素组成】C 48.11% H 6.63% B 3.09% Br 22.86% Cl 10.14% O 9.16%

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：(VI)

The preparation of the intermediate aminoboronate (VII) is shown in Scheme 27968701a. Addition of catecholborane (II) to allyl bromide (I) provided boronic ester (III). Subsequent exchange with (+)-alpha-pinanediol (IV) afforded the chiral borane (V). Insertion of dichloromethyllithium in (V) produced the alpha-chloroboronic ester (VI). The required amino compound was then obtained by displacement of the halogen with lithium hexamethyldisilazide, followed by acid-catalyzed desilylation.

参考文献中间体

合成目标

【1】 Verbeuren, T.; Rupin, A.; De Nanteuil, G.; Gloanec, P.; New dicarbonyl cycloalkyl based thrombin inhibitors with improved activity and selectivity compared to (D)-Phe-Pro-boroArg derivatives . 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 201.

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)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(II)	32533	1,3,2-benzodioxaborole	274-07-7	C₆H₅BO₂	详情	详情
(III)	35558	2-(3-bromopropyl)-1,3,2-benzodioxaborole		C₉H₁₀BBrO₂	详情	详情
(IV)	32535	(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol		C₁₀H₁₈O₂	详情	详情
(V)	35559	(1R,2S,6R,8R)-4-(3-bromopropyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane		C₁₃H₂₂BBrO₂	详情	详情
(VI)	35560	(1R,2S,6R,8R)-4-[(1S)-4-bromo-1-chlorobutyl]-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane		C₁₄H₂₃BBrClO₂	详情	详情
(VII)	35561	(1R)-4-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]-1-butanamine; (1R)-4-bromo-1-[(1R,2S,6R,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylamine		C₁₄H₂₅BBrNO₂	详情	详情

Extended Information