(2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methyl-5-hexen-3-ol | 203926-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methyl-5-hexen-3-ol
• 英文别名: (2R,3S)-1-(4-methoxybenzyloxy)-2-methylhex-5-en-3-ol；(2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methylhex-5-en-3-ol
• CAS: 203926-55-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: UWQKSPAAVZFFOQ-DOMZBBRYSA-N

物化性质

• 沸点：
  376.4±37.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methyl-5-hexen-3-ol 在 咪唑 、 chromium dichloride 、 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 sodium periodate 、 四氧化锇 、 二苯基磷酸 、 四丁基氟化铵 、 水 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 达卡巴嗪 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 desepoxyarenastatin A
  参考文献：
  名称：

  A concise synthesis of the cytotoxic depsipeptide arenastatin A

  摘要：

  Arenastatin A (1, cryptophycin 24) was synthesized by convergence of hydroxy eater 16 with amino acid derivative 27; two independent and highly efficient routes to 16 are disclosed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02014-0
• 作为产物：
  描述：

  烯丙基三丁基锡 、 (2R)-3-[(4-甲氧基苯基)甲氧基]-2-甲基丙醛 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(2R,3S)-1-[(4-methoxyphenyl)methoxy]-2-methyl-5-hexen-3-ol
  参考文献：
  名称：

  A concise synthesis of the cytotoxic depsipeptide arenastatin A

  摘要：

  Arenastatin A (1, cryptophycin 24) was synthesized by convergence of hydroxy eater 16 with amino acid derivative 27; two independent and highly efficient routes to 16 are disclosed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02014-0

文献信息

• [EN] NOVEL CRYPTOPHYCIN COMPOUNDS AND CONJUGATES, THEIR PREPARATION AND THEIR THERAPEUTIC USE<br/>[FR] NOUVEAUX COMPOSÉS ET CONJUGUÉS DE CRYPTOPHYCINE, LEUR PRÉPARATION ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：SANOFI SA

  公开号：WO2017076998A1

  公开（公告）日：2017-05-11

  The present invention relates to cryptophycin compounds of formula (I). The invention also relates to cryptophycin payloads, to cryptophycin conjugates, to compositions containing them and to their therapeutic use, especially as anticancer agents. The invention also relates to the process for preparing these conjugates.

  本发明涉及公式（I）的隐藻素化合物。该发明还涉及隐藻素有效载荷、隐藻素偶联物、含有它们的组合物及其治疗用途，尤其是作为抗癌剂。该发明还涉及制备这些偶联物的过程。
• Versatile Synthesis of the C3−C14 Domain of 7-Deoxyokadaic Acid
  作者：Timothy M. Trygstad、Yucheng Pang、Craig J. Forsyth

  DOI：10.1021/jo8017457

  日期：2009.1.16

  Described is a flexible synthesis of the C3−C14 domain of 7-deoxyokadaic acid that is amenable to facile structural diversification. Treatment of ynone 10 under acidic conditions led to net bis-conjugate addition of the latent diol to give the thermodynamically favored spiroketal 27, a versatile intermediate, en route to 7-deoxyokadaic acid and analogs.

  描述了适合于容易的结构多样化的7-脱氧冈田酸的C3-C14结构域的灵活合成。在酸性条件下对炔酮10的处理导致了潜在二醇的净双共轭加成，从而获得了热力学上有利的螺环酮27，这是一种通用的中间体，可直接通往7-脱氧冈田酸和类似物。
• Fit-for-Purpose Synthesis of an Aza-Cryptophycin Analogue as the Payload for an Antibody–Drug Conjugate
  作者：Audrey Bendelac、Françoise Benedetti、Valerie Doublet-Decabras、Rachel Lokovi、François Decalogne、Antony Bigot

  DOI：10.1021/acs.oprd.2c00080

  日期：2022.8.19

  The synthesis of an aza-cryptophycin analogue is described, featuring a highly trans-selective ring-closing metathesis reaction and an asymmetric Corey–Chaykovsky-type reaction to install the epoxide function. This latter reaction is an answer to the long-standing synthetic challenged posed by the efficient formation of the epoxide function of the cryptophycin family of compounds in a diastereoselective

  描述了氮杂隐藻素类似物的合成，具有高度反式选择性闭环复分解反应和不对称 Corey-Chaykovsky 型反应以安装环氧化物功能。后一种反应是对由以非对映选择性方式有效形成隐藻素家族化合物的环氧化物功能所带来的长期合成挑战的答案。与之前使用的合成（27 到 19 步）相比，它允许步骤数减少三分之一，并将最长线性序列的总产率提高 27 倍（0.6% 到 16%）。这种适合目的的合成允许为基于隐藻素的抗体-药物偶联计划的早期阶段稳定供应材料。
• Cryptophycin compounds and conjugates, their preparation and their therapeutic use
  申请人：SANOFI

  公开号：US10941139B2

  公开（公告）日：2021-03-09

  The present invention relates to cryptophycin compounds of formula (I). The invention also relates to cryptophycin payloads, to cryptophycin conjugates, to compositions containing them and to their therapeutic use, especially as anticancer agents. The invention also relates to the process for preparing these conjugates.

  本发明涉及式（I）的隐球霉素化合物。本发明还涉及隐球菌苷有效载荷、隐球菌苷共轭物、含有它们的组合物及其治疗用途，特别是作为抗癌剂。本发明还涉及制备这些共轭物的工艺。
• Synthetic Studies toward the C32–C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36–C42 Subunit
  作者：Simon Specklin、Guillaume Boissonnat、Camille Lecourt、Geoffroy Sorin、Marie-Isabelle Lannou、Janick Ardisson、François Sautel、Georges Massiot、Christophe Meyer、Janine Cossy

  DOI：10.1021/acs.orglett.5b00955

  日期：2015.5.15

  The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an alpha,beta-unsaturated delta-lactone followed by alpha- hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the H-1 and C-13 NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit.