(1'S,3R)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran | 138535-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1'S,3R)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran
• 英文别名: (1S,3'S)-tert-butyl [1-(8'-methoxy-1'-oxoisochroman-3'-yl)-3-methylbutyl]carbamate；(3R)-3-[(1'S)-tert-butoxycarbonylamino-3'-methylbutyl]-8-methoxy-3,4-dihydroisocoumarin；tert-butyl N-[(1S)-1-[(3R)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]carbamate
• CAS: 138535-46-3
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: JICMYFMZAGTPQL-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,3R)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran 在 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 1-羟基苯并三唑 、 甲基磺酰氯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 magnesium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S',3S,4''S)-(E)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4''-<(benzyloxycarbonyl)amino>-5''-(benzyloxycarbonyl)-pent-2-enamide
  参考文献：
  名称：

  AI-77-B的全合成

  摘要：

  报道了AI-77-B（1）的短总合成，该合成使用S-亮氨酸和S-天冬氨酸作为光学活性原料生产了天然对映体。

  DOI：

  10.1016/s0040-4039(00)92088-4
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 正丁基锂 、 三氧化硫吡啶 、 magnesium bromide ethyl etherate 、 三乙胺 、 二异丙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.33h， 生成 (1'S,3R)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran
  参考文献：
  名称：

  胃保护性天然产物AI-77-B和盐酸氨苄青霉素C的天然对映异构体的全合成

  摘要：

  描述了AI-77-B的天然对映异构体和氨苄青霉素C盐酸盐的全合成。

  DOI：

  10.1016/0040-4020(95)00776-5

文献信息

• Asymmetric Total Synthesis of the Gastroprotective Microbial Agent AI-77-B
  作者：Arun K. Ghosh、Alexander Bischoff、John Cappiello

  DOI：10.1002/ejoc.200390125

  日期：2003.3

  An enantioselective total synthesis of the pseudopeptide microbial agent AI-77-B, which has shown potent antiulcerogenic properties, is described. The synthesis is convergent and involves the assembly of a dihydroisocoumarin fragment and a hydroxy amino acid. The dihydroisocoumarin derivative was synthesised by means of a Diels-Alder reaction between 1-methoxy-1,3-cyclohexadiene and an alkynyl ester

  描述了伪肽微生物制剂 AI-77-B 的对映选择性全合成，该制剂显示出有效的抗溃疡特性。该合成是收敛的，涉及二氢异香豆素片段和羟基氨基酸的组装。二氢异香豆素衍生物是通过1-甲氧基-1,3-环己二烯与作为亲二烯体的炔酯衍生物之间的Diels-Alder反应合成的。炔基酯是通过两种不同的合成路线立体选择性地获得的：(1)亮氨酸的立体选择性烯丙基化，以及(2)钛烯醇化物介导的与三氯丁醛(一种新型高炔丙醛等价物)的抗羟醛反应。羟基氨基酸部分的立体中心是通过钛烯醇化物介导的顺醛醇反应、Curtius重排和Dondoni醛同系化的应用产生的。二氢异香豆素和羟基氨基酸部分缩合，随后除去保护基团，得到光学活性的AI-77-B。
• A total synthesis of AI-77-B
  作者：Richard A. Ward、Garry Procter

  DOI：10.1016/s0040-4039(00)92088-4

  日期：1992.6

  A short total synthesis of AI-77-B (1) is reported, which produces the natural enantiomer using S-leucine and S-aspartic acid as the optically active starting materials.

  报道了AI-77-B（1）的短总合成，该合成使用S-亮氨酸和S-天冬氨酸作为光学活性原料生产了天然对映体。
• Original preparation of conjugates for antibody production against Amicoumacin-related anti-microbial agents
  作者：Svitlana Shinkaruk、Bernard Bennetau、Pierre Babin、Jean-Marie Schmitter、Valerie Lamothe、Catherine Bennetau-Pelissero、Maria C. Urdaci

  DOI：10.1016/j.bmc.2008.08.017

  日期：2008.10

  Amicoumacins are natural products with potent anti-ulcerogenic and anti-bacterial activities, and have been isolated from different Bacillus genera. They belong to a family of 3,4-dihydroisocoumarin derivatives bearing hydroxylated amino acid side chains. The 3,4-dihydroisocoumarin moiety of Amicoumacins has been obtained in two steps from 2-methoxybenzoic acid by combining directed and benzylic metalation strategies. The use of s-BuLi in both steps gave satisfactory and reproducible yields. For the development of an immunoassay (ELISA) of Amicoumacin-related compounds in biological media, the deprotected 3,4-dihydroisocoumarin moiety has been coupled to the BSA carrier protein via a homo-bifunctional linker deriving from D-tartaric acid. This approach enabled to introduce the hydroxylated portion of Amicoumacin directly during the preparation of hapten-protein conjugates. The coupling ratio was evaluated by mass spectrometry. The hapten-protein conjugate showing the best coupling ratio was used to generate polyclonal immunosera in rabbits. After immunoserum titration, ELISA conditions were set up and specificity tests were performed on solutions of pure parent compounds, semi-purified Amicoumacin B as well as on culture supernatants of strains known for their Amicoumacin production. This immunoassay is suitable for a rapid and simple screening test for the production of Amicoumacins and its related compounds by bacterial strains. (c) 2008 Elsevier Ltd. All rights reserved.
• A Total Synthesis of the Natural Enantiomer of the Gastroprotective Natural Products AI-77-B and Amicoumacin C Hydrochloride
  作者：Richard A. Ward、Garry Procter

  DOI：10.1016/0040-4020(95)00776-5

  日期：1995.11

  A total synthesis of the natural enantiomer of AI-77-B and amicoumacin C hydrochloride is described.

  描述了AI-77-B的天然对映异构体和氨苄青霉素C盐酸盐的全合成。