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【结 构 式】 
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【分子编号】42022 【品名】methyl (2S,3R)-2-[[2-(benzyloxy)-5-methoxybenzoyl]amino]-3-hydroxybutanoate 【CA登记号】 |
【 分 子 式 】C20H23NO6 【 分 子 量 】373.40576 【元素组成】C 64.33% H 6.21% N 3.75% O 25.71% |
合成路线1
该中间体在本合成路线中的序号：(IX)Synthesis of intermediate (XII): The protection of 2-hydroxy-5-methoxybenzoic acid (VI) with benzyl bromide and K2CO3 in DMF gives 2-(benzyloxy)-5-methoxybenzoic acid (VII), which is condensed with L-threonine methyl ester (VIII) by means of (OEt)2P(O)CN (DEPC) and TEA in DMF yielding the corresponding benzamide (IX). The oxidation of (IX) with DMP, followed by cyclization by means of PPh3 and TEA affords 2-[2-(benzyloxy)-5-methoxyphenyl]-5-methyloxazole-4-carboxylic acid methyl ester (X) which is debenzylated with H2 over Pd/C in methanol to the corresponding phenol (XI). Finally the ester group of (XI) is hydrolyzed with NaOH in THF/water to afford the acid intermediate (XII).
| 【1】 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 |
|---|---|---|---|---|---|---|
| (VI) | 42020 | 2-hydroxy-5-methoxybenzoic acid | 2612-02-4 | C8H8O4 | 详情 | 详情 |
| (VII) | 42021 | 2-(benzyloxy)-5-methoxybenzoic acid | C15H14O4 | 详情 | 详情 | |
| (VIII) | 42026 | methyl (2S,3R)-2-amino-3-hydroxybutanoate | C5H11NO3 | 详情 | 详情 | |
| (IX) | 42022 | methyl (2S,3R)-2-[[2-(benzyloxy)-5-methoxybenzoyl]amino]-3-hydroxybutanoate | C20H23NO6 | 详情 | 详情 | |
| (X) | 42023 | methyl 2-[2-(benzyloxy)-5-methoxyphenyl]-5-methyl-1,3-oxazole-4-carboxylate | C20H19NO5 | 详情 | 详情 | |
| (XI) | 42024 | methyl 2-(2-hydroxy-5-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylate | C13H13NO5 | 详情 | 详情 | |
| (XII) | 42025 | 2-(2-hydroxy-5-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylic acid | C12H11NO5 | 详情 | 详情 |