(1'S,3S)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran | 138535-45-2

• 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,3S)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran
• 英文别名: (3S)-3-[(1'S)-tert-butoxycarbonylamino-3'-methylbutyl]-8-methoxy-3,4-dihydroisocoumarin；tert-butyl N-[(1S)-1-[(3S)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]carbamate
• CAS: 138535-45-2
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: JICMYFMZAGTPQL-HOCLYGCPSA-N

物化性质

• 熔点：
  138-145 °C
• 沸点：
  534.5±50.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

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,3S)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-8-methoxy-1H-2-benzopyran 在 碘 、 magnesium 作用下， 以 苯 为溶剂， 反应 1.0h， 以58%的产率得到(1'S,3S)-3-<1'-(tert-butyloxycarbonylamino)-3'-methylbutyl>-3,4-dihydro-8-hydroxy-1-oxo-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
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 氢氧化钾 、 sodium hydroxide 、 正丁基锂 、 三氧化硫吡啶 、 magnesium bromide ethyl etherate 、 甲基磺酰氯 、 三乙胺 、 二异丙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 6.33h， 生成 (1'S,3S)-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

• 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。
• A New Enantioselective Synthesis of the Aminodihydroisocoumarin Moiety of AI-77-B
  作者：Hiyoshizo Kotsuki、Aya Miyazaki、Masamitsu Ochi

  DOI：10.1246/cl.1992.1255

  日期：1992.7

  The aminodihydroisocoumarin moiety of AI-77-B, a gastroprotective substance isolated from Bacillus pumilus AI-77, has been prepared from a convenient chiral synthon of L-erythrose by combination of chiral triflate technology and regioselective aromatic carboxylation.

  AI-77-B 是一种从枯草杆菌 AI-77 中分离出来的胃保护物质，它的氨基二氢异香豆素分子是通过手性三酸酯技术和区域选择性芳香羧化技术相结合，从 L-erythrose 的简便手性合成物中制备出来的。
• Stereoselective Synthesis of Pseudopeptide Microbial Agent AI-77-B
  作者：Arun K. Ghosh、Alexander Bischoff、John Cappiello

  DOI：10.1021/ol0101279

  日期：2001.8.1

  [GRAPHICS]An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.
• 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。