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【结 构 式】

【分子编号】42031

【品名】benzyl (3S)-1-[[tert-butyl(diphenyl)silyl]oxy]-2-oxoazepanylcarbamate

【CA登记号】

【 分 子 式 】C30H36N2O4Si

【 分 子 量 】516.71242

【元素组成】C 69.74% H 7.02% N 5.42% O 12.39% Si 5.44%

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:(XVIII)

Synthesis of the final product: The cyclization of L-lysine (XVII) according to Miller et al. gives cyclic hydroxamate (XVIII), which is deprotected by hydrogenation with H2 over Pd/C in MeOH yielding 3-amino-1-(tert-butyldiphenylsilyloxy)perhydroazepin-2-one (XIX). The condensation of (XIX) with acid intermediate (V) by means of DEPC and TEA in DMF affords the corresponding amide (XX), which is esterified at its free OH group with acid intermediate (XVI) by means of DCC and DMAP in toluene to provide the ester (XXI). The deprotection of (XXI) with H2 over Pd/C in MeOH gives the amine (XXII), which is acylated with acid intermediate (XII) by means of EDC in CH2Cl2 to furnish the corresponding amide (XXIII). Finally this compound is deprotected with trifluoroacetic acid in CH2Cl2 to give the title product.

1 Miller, M.J.; Hu, J.; Total synthesis of a mycobactin S, a siderophore and growth promoter of Mycobacterium smegmatis, and determination of its growth inhibitory activity against Mycobacterium tuberculosis. J Am Chem Soc 1997, 119, 15, 3462.
2 Yokokawa, F.; et al.; Total synthesis of amamistatin A, an antiproliferative linear peptide from an actinomycete. Tetrahedron 2000, 56, 19, 3027.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 42019 (3S)-3-hydroxy-2,2-dimethyldecanoic acid C12H24O3 详情 详情
(XII) 42025 2-(2-hydroxy-5-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylic acid C12H11NO5 详情 详情
(XVI) 42030 (12R)-12-[[(benzyloxy)carbonyl]amino]-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatridecan-13-oic acid C20H32N2O7Si 详情 详情
(XVII) 17525 (2S)-6-amino-2-[[(benzyloxy)carbonyl]amino]hexanoic acid C14H20N2O4 详情 详情
(XVIII) 42031 benzyl (3S)-1-[[tert-butyl(diphenyl)silyl]oxy]-2-oxoazepanylcarbamate C30H36N2O4Si 详情 详情
(XIX) 42032 (3S)-3-amino-1-[[tert-butyl(diphenyl)silyl]oxy]-2-azepanone C22H30N2O2Si 详情 详情
(XX) 42033 (3S)-N-((3S)-1-[[tert-butyl(diphenyl)silyl]oxy]-2-oxoazepanyl)-3-hydroxy-2,2-dimethyldecanamide C34H52N2O4Si 详情 详情
(XXI) 42034 (1S)-1-[2-[((3S)-1-[[tert-butyl(diphenyl)silyl]oxy]-2-oxoazepanyl)amino]-1,1-dimethyl-2-oxoethyl]octyl (12R)-12-[[(benzyloxy)carbonyl]amino]-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatridecan-13-oate C54H82N4O10Si2 详情 详情
(XXII) 42035 (1S)-1-[2-[((3S)-1-[[tert-butyl(diphenyl)silyl]oxy]-2-oxoazepanyl)amino]-1,1-dimethyl-2-oxoethyl]octyl (12R)-12-amino-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatridecan-13-oate C46H76N4O8Si2 详情 详情
(XXIII) 42036 (1S)-1-[2-[((3S)-1-[[tert-butyl(diphenyl)silyl]oxy]-2-oxoazepanyl)amino]-1,1-dimethyl-2-oxoethyl]octyl (12R)-8-formyl-12-([[2-(2-hydroxy-5-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]carbonyl]amino)-2,2-dimethyl-5,7-dioxa-8-aza-2-silatridecan-13-oate C58H85N5O12Si2 详情 详情
Extended Information