• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】57925

【品名】methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-hexenoate

【CA登记号】

【 分 子 式 】C12H21NO4

【 分 子 量 】243.30308

【元素组成】C 59.24% H 8.7% N 5.76% O 26.3%

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:(VI)

The enantioselective alkylation of the nickel complex (I) of the Schiff base derived from glycine and (S)-2-[N'-(N-benzylprolyl)amino]benzophenone with 4-bromo-1-butene (II) affords the corresponding complex (III) of (S)-2-amino-5-hexenoic acid, which is subsequently hydrolyzed to the free aminoacid (IV) under mild acidic conditions. Esterification of (IV) by means of SOCl2 in methanol leads to amino ester (V), and further protection with di-tert-butyl dicarbonate provides the N-Boc derivative (VI). Hydroboration of the double bond of (VI) with diisopinocampheylborane, followed by in situ oxidation with acetaldehyde gives rise to the diethyl boronate (VII). This is then converted to the isolable pinanediol boronate (IX) upon treatment with (+)-pinanediol (VIII). Finally, total deprotection of (IX) by refluxing with 12 M HCl furnishes the title compound.

1 Collet, S.; et al.; Synthesis and evaluation of omega-borono-alpha-amino acids as active-site probes of arginase and nitric oxide synthases. J Chem Soc - Perkins Trans I 2000, 2, 177.
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) 57921   C27H25N3NiO3 详情 详情
(II) 11720 4-Bromo-1-butene 5162-44-7 C4H7Br 详情 详情
(III) 57922   C31H31N3NiO3 详情 详情
(IV) 57923 (2S)-2-amino-5-hexenoic acid C6H11NO2 详情 详情
(V) 57924 methyl (2S)-2-amino-5-hexenoate C7H13NO2 详情 详情
(VI) 57925 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-hexenoate C12H21NO4 详情 详情
(VII) 57926 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-6-(diethoxyboryl)hexanoate C16H32BNO6 详情 详情
(VIII) 16644 (-)-Pinanediol; (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol 20536-52-1 C10H18O2 详情 详情
(IX) 57927 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-6-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]hexanoate C22H38BNO6 详情 详情
Extended Information