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【结 构 式】 
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【分子编号】61235 【品名】methyl (3R)-6-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]hexanoate 【CA登记号】 |
【 分 子 式 】C20H30N2O6 【 分 子 量 】394.46808 【元素组成】C 60.9% H 7.67% N 7.1% O 24.34% |
合成路线1
该中间体在本合成路线中的序号：(III)In a closely related method, N5-(benzyloxycarbonyl)-N2-Boc-(R)-ornithine (I) is coupled to diazomethane, via activation with isobutyl chloroformate, to afford the diazo ketone (II). Rearrangement of (II) in the presence of silver benzoate gives the beta-lysine derivative (III). After saponification of the methyl ester (III), the resultant carboxylic acid (IV) is coupled to benzyl 1-methylhydrazinoacetate (V) yielding hydrazide (VI). Hydrogenolysis of the N-carbobenzoxy groups of (VI) provides the Boc-protected precursor (VII), which is finally deprotected to the title compound under acidic conditions.
| 【1】 Raju, B.; Anandan, S.K.; Gu, S.; et al. ; Conformationally restricted analogs of deoxynegamycin. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1684. |
| 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) | 61233 | (2R)-5-{[(benzhydryloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoic acid | C24H30N2O6 | 详情 | 详情 | |
| (II) | 61234 | C19H26N4O5 | 详情 | 详情 | ||
| (III) | 61235 | methyl (3R)-6-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]hexanoate | C20H30N2O6 | 详情 | 详情 | |
| (IV) | 61236 | (3R)-6-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]hexanoic acid | C19H28N2O6 | 详情 | 详情 | |
| (V) | 61237 | benzyl 2-(1-methylhydrazino)acetate | C10H14N2O2 | 详情 | 详情 | |
| (VI) | 61238 | benzyl 2-(2-{(3R)-6-{[(benzhydryloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]hexanoyl}-1-methylhydrazino)acetate | C35H44N4O7 | 详情 | 详情 | |
| (VII) | 61239 | 2-(2-{(3R)-6-amino-3-[(tert-butoxycarbonyl)amino]hexanoyl}-1-methylhydrazino)acetic acid | C14H28N4O5 | 详情 | 详情 |