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【结 构 式】 
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【分子编号】61230 【品名】methyl (3R)-3,6-bis{[(benzyloxy)carbonyl]amino}hexanoate 【CA登记号】 |
【 分 子 式 】C23H28N2O6 【 分 子 量 】428.4852 【元素组成】C 64.47% H 6.59% N 6.54% O 22.4% |
合成路线1
该中间体在本合成路线中的序号：(III)In an alternative method, N,N'-bis-(benzyloxycarbonyl)-(R)-ornithine (I) is treated with PCl5 to afford the corresponding acid chloride, which is then converted to diazo ketone (II) with ethereal diazomethane. Rearrangement of (II) under Arndt-Eistert conditions in the presence of silver benzoate leads to the beta-lysine derivative (III). After saponification of the methyl ester (III), the resultant carboxylic acid (IV) is coupled to ethyl 1-methylhydrazinoacetate (V) via the mixed anhydride with isobutyl chloroformate, to give hydrazide (VI). Alkaline hydrolysis of the ethyl ester (VI) yields acid (VII). The N-carbobenzoxy groups are finally removed by hydrogenolysis to furnish the title compound.
| 【1】 Curran, W.V.; Boothe, J.H.; The synthesis of deoxynegamycin and some related compounds. J Antibiot 1978, 31, 9, 914. |
| 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) | 61228 | (2R)-2,5-bis{[(benzyloxy)carbonyl]amino}pentanoic acid | C21H24N2O6 | 详情 | 详情 | |
| (II) | 61229 | C22H24N4O5 | 详情 | 详情 | ||
| (III) | 61230 | methyl (3R)-3,6-bis{[(benzyloxy)carbonyl]amino}hexanoate | C23H28N2O6 | 详情 | 详情 | |
| (IV) | 61219 | (3R)-3,6-bis{[(benzyloxy)carbonyl]amino}hexanoic acid | C22H26N2O6 | 详情 | 详情 | |
| (V) | 61231 | ethyl 2-(1-methylhydrazino)acetate | C5H12N2O2 | 详情 | 详情 | |
| (VI) | 61232 | ethyl 2-[2-((3R)-3,6-bis{[(benzyloxy)carbonyl]amino}hexanoyl)-1-methylhydrazino]acetate | C27H36N4O7 | 详情 | 详情 | |
| (VII) | 61222 | 2-[2-((3R)-3,6-bis{[(benzyloxy)carbonyl]amino}hexanoyl)-1-methylhydrazino]acetic acid | C25H32N4O7 | 详情 | 详情 |