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【结 构 式】

【分子编号】36657

【品名】3-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]propyl azide; (1S,2R,6S,8S)-4-(3-azidopropyl)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane

【CA登记号】

【 分 子 式 】C13H22BN3O2

【 分 子 量 】263.1477

【元素组成】C 59.34% H 8.43% B 4.11% N 15.97% O 12.16%

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 hydroboration of allyl bromide (I) with diisopinocampheylborane gives the 3-bromopropylboronic ester (II), which by treatment with acetaldehyde and water yields the boronic acid (III). The reaction of (III) with NaN3 and ethanol affords 3-azidoboronic acid ethyl ester (IV), which is transesterified with optically active pipanediol (V) giving the cyclic ester (VI). The homologation of (VI) with LDA, ZnCl2 and dichloromethane in THF yields the alpha-chlorobutylboronic ester (VII), which is aminated with hexamethyldisylazane (HMDS) and BuLi to provide the silylated alpha-aminoboronic ester (VIII). The desilylation of (VIII) with methanol, and its protection with benzyl chloroformate gives the protected alpha-aminoboronic ester (IX). The hydrogenation of the azido group of (IX) with H2 over PtO2 affords the 4-aminobutylboronic ester (X), which is treated with N,N'-bis(tert-butoxycarbonyl)thiourea (XI), HgCl2 and TEA in DMF to give the guanidine derivative (XII). Finally, this compound is hydrolyzed and deprotected with refluxing 6N HCl.

1 Lebarbier, C.; Carreaux, F.; Carboni, B.; Boucher, J.L.; Synthesis of boronic acid analogs of L-arginine as alternate substrates or inhibitors of nitric oxide synthase. Bioorg Med Chem Lett 1998, 8, 18, 2573.
2 Lebarbier, C.; et al.; Synthesis of a boronic acid analogue of L-ornithine. Synthesis 1996, 1371.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(I) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(II) 36654 bis[[(1R,2S,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methyl] 3-bromopropylboronate C25H44BBrO2 详情 详情
(III) 36655 3-bromopropylboronic acid C3H8BBrO2 详情 详情
(IV) 36656 diethyl 3-azidopropylboronate C7H16BN3O2 详情 详情
(V) 32535 (1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol C10H18O2 详情 详情
(VI) 36657 3-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]propyl azide; (1S,2R,6S,8S)-4-(3-azidopropyl)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane C13H22BN3O2 详情 详情
(VII) 36658 (4S)-4-chloro-4-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl azide; (1S,2R,6S,8S)-4-[(1S)-4-azido-1-chlorobutyl]-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]decane C14H23BClN3O2 详情 详情
(VIII) 36659 N-[(1R)-4-azido-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl](trimethyl)-N-(trimethylsilyl)silanamine; N-[(1R)-4-azido-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butyl]-N,N-bis(trimethylsilyl)amine C20H41BN4O2Si2 详情 详情
(IX) 36660 benzyl (1R)-4-azido-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylcarbamate C22H31BN4O4 详情 详情
(X) 36661 benzyl (1R)-4-amino-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylcarbamate C22H33BN2O4 详情 详情
(XI) 21843 tert-butyl [(tert-butoxycarbonyl)amino]carbothioylcarbamate 145013-05-4 C11H20N2O4S 详情 详情
(XII) 36662 benzyl (1R)-4-([[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl]amino)-1-[(1S,2R,6S,8S)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl]butylcarbamate C33H51BN4O8 详情 详情
Extended Information