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【结 构 式】

【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%

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:(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
Extended Information