【结 构 式】 |
【分子编号】61227 【品名】methyl 2-[2-((3S)-3,6-bis{[(benzyloxy)carbonyl]amino}-5-iodohexanoyl)-1-methylhydrazino]acetate 【CA登记号】 |
【 分 子 式 】C26H33IN4O7 【 分 子 量 】640.47525 【元素组成】C 48.76% H 5.19% I 19.81% N 8.75% O 17.49% |
合成路线1
该中间体在本合成路线中的序号:(VI)In a different procedure, starting from negamycin (I), protection with benzyl S-(4,6-dimethylpyrimidin-2-yl)thiol carbonate (II) yields the bis-(benzyloxycarbonyl) derivative (III). Subsequent esterification of acid (III) employing diazomethane leads to methyl ester (IV). The free hydroxyl group of (IV) is then converted to the mesylate (V) by means of methanesulfonyl chloride in cold pyridine. Further mesylate group displacement in (V) with NaI gives rise to the alkyl iodide (VI). Finally, simultaneous cleavage of the N-carbobenzoxy groups and iodide hydrogenolysis in (VI) is accomplished by hydrogenation in the presence of Pd/BaCO3.
【1】 Umezawa, H.; Kondo, S. (Microbial Chemistry Research Foundation); delta-Substd. negamycin derivs. and syntheses. US 4065495 . |
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) | 61223 | 2-{2-[(3R,5R)-3,6-diamino-5-hydroxyhexanoyl]-1-methylhydrazino}acetic acid | C9H20N4O4 | 详情 | 详情 | |
(II) | 32266 | O-benzyl S-(4,6-dimethyl-2-pyrimidinyl) carbonothioate; benzyl S-4,6-dimethylpyrimidin-2-ylthiolcarbonate | C14H14N2O2S | 详情 | 详情 | |
(III) | 61224 | 2-[2-((3R,5R)-3,6-bis{[(benzyloxy)carbonyl]amino}-5-hydroxyhexanoyl)-1-methylhydrazino]acetic acid | C25H32N4O8 | 详情 | 详情 | |
(IV) | 61225 | methyl 2-[2-((3R,5R)-3,6-bis{[(benzyloxy)carbonyl]amino}-5-hydroxyhexanoyl)-1-methylhydrazino]acetate | C26H34N4O8 | 详情 | 详情 | |
(V) | 61226 | methyl 2-(2-{(3R,5R)-3,6-bis{[(benzyloxy)carbonyl]amino}-5-[(methylsulfonyl)oxy]hexanoyl}-1-methylhydrazino)acetate | C27H36N4O10S | 详情 | 详情 | |
(VI) | 61227 | methyl 2-[2-((3S)-3,6-bis{[(benzyloxy)carbonyl]amino}-5-iodohexanoyl)-1-methylhydrazino]acetate | C26H33IN4O7 | 详情 | 详情 |