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【结 构 式】

【分子编号】31061

【品名】methyl 3-(benzylamino)dodecanoate

【CA登记号】

【 分 子 式 】C20H33NO2

【 分 子 量 】319.48756

【元素组成】C 75.19% H 10.41% N 4.38% O 10.02%

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:(IV)

The Wittig condensation of decanal (I) with phosphorane (II) in benzene gives trans-2-dodecenoic acid methyl ester (III), which by thermal Michael addition of benzylamine yields the protected beta-aminoester (IV). The debenzylation of (IV) with H2 over Pd/C in methanol affords the free aminoester (V), which is condensed with N-(tert-butoxycarbonyl)-L-valine (VI) by means of 1-[3-(dimethylamino)propyl]-1-ethyl carbodiimide (WSC) in dichloromethane to give the dipeptide (VII) as a diastereomeric mixture, from which the desired isomer (VIII) is isolated by crystallization. The deprotection of the amino group of (VIII) with TFA in dichloromethane affords the peptide (IX), which is coupled with the conveniently protected glycyl-L-lysine dipeptide (X) by means of WSC as before to give the tetrapeptide (XI). The hydrolysis of the methyl ester group of (XI) with LiOH in THF/methanol/water yields the acidic tetrapeptide (XII). The intermediate glycyl-L-lysine dipeptide (X) has been obtained by coupling N-(tert-butoxycarbonyl)glycine (XV) with Nomega-(benzyloxycarbonyl)-L-lysine methyl ester (XVI) by means of WSC as before to give dipeptide (XVI), which is submitted to alkaline hydrolysis to provide the intermediate dipeptide (X).

1 Sakai, K.; Yoshioka, T.; Agematu, H.; Chiba, H.; Dobashi, K.; Rhodopeptins, novel cyclic tetrapeptides with antifungal activities from Rhodococcus sp. III. Synthetic study of rhodopeptins. J Antibiot 1999, 52, 8, 710.
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) 31059 decanal 112-31-2 C10H20O 详情 详情
(II) 14686 2-phenyl-1,3-dioxane C10H12O2 详情 详情
(III) 31060 methyl (E)-2-dodecenoate C13H24O2 详情 详情
(IV) 31061 methyl 3-(benzylamino)dodecanoate C20H33NO2 详情 详情
(V) 31062 methyl 3-aminododecanoate C13H27NO2 详情 详情
(VI) 19733 (2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid C10H19NO4 详情 详情
(VII) 31063 methyl 3-([(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]amino)dodecanoate C23H44N2O5 详情 详情
(VIII) 31064 methyl (3R)-3-([(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]amino)dodecanoate C23H44N2O5 详情 详情
(IX) 31065 methyl (3R)-3-[[(2S)-2-amino-3-methylbutanoyl]amino]dodecanoate C18H36N2O3 详情 详情
(X) 31066 (2S)-6-[[(benzyloxy)carbonyl]amino]-2-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)hexanoic acid C21H31N3O7 详情 详情
(XI) 31067 methyl (9S,12S,15R)-9-(4-[[(benzyloxy)carbonyl]amino]butyl)-12-isopropyl-2,2-dimethyl-15-nonyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazaheptadecan-17-oate C39H65N5O9 详情 详情
(XII) 31068 (9S,12S,15R)-9-(4-[[(benzyloxy)carbonyl]amino]butyl)-12-isopropyl-2,2-dimethyl-15-nonyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazaheptadecan-17-oic acid C38H63N5O9 详情 详情
(XV) 18066 N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid 4530-20-5 C7H13NO4 详情 详情
(XVI) 31069 methyl (2S)-2-amino-6-[[(benzyloxy)carbonyl]amino]hexanoate C15H22N2O4 详情 详情
(XVII) 31070 methyl (2S)-6-[[(benzyloxy)carbonyl]amino]-2-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)hexanoate C22H33N3O7 详情 详情
Extended Information