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【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.

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
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