(+)-conduritol C | 133319-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-conduritol C
• 英文别名: (1S,2S,3R,4S)-cyclohex-5-ene-1,2,3,4-tetrol
• CAS: 133319-93-4
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: LRUBQXAKGXQBHA-OMMKOOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alpha-D-半乳糖 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 硫酸 、 mercury(II) diacetate 、 碘 、 sodium methylate 、 sodium hydride 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 六甲基磷酰三胺 、 水 、 丙酮 、 甲苯 为溶剂， 反应 15.42h， 生成 (+)-conduritol C
  参考文献：
  名称：

  Mereyala, Hari Babu; Gaddam, Reddy, Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2187 - 2190

  摘要：

  DOI：

文献信息

• Integrated synthesis of conduritols A–F using a single chiral building block
  作者：Masatoshi Honzumi、Kou Hiroya、Takahiko Taniguchi、Kunio Ogasawara

  DOI：10.1039/a905462f

  日期：——

  Six possible diastereomers of conduritols have been synthesized diastereoselectively in an integrated manner starting from a single chiral precursor, which served as a synthetic equivalent of chiral cis-1,4-dihydroxycyclohexa-2,5-diene.

  从作为手性顺式-1,4-二羟基环己-2,5-二烯的合成等效物的单一手性前体开始，我们以综合方式非对映选择性地合成了六种可能的缩酮非对映异构体。
• Facile Syntheses of All Possible Diastereomers of Conduritol and Various Derivatives of Inositol Stereoisomers in High Enantiopurity from <i>m</i><i>yo</i>-Inositol
  作者：Yong-Uk Kwon、Changgook Lee、Sung-Kee Chung

  DOI：10.1021/jo016237a

  日期：2002.5.1

  Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their

  基于磷酸肌醇的信号传导过程在细胞内信号转导事件中至关重要。肌醇磷酸酯类似物可用于探测肌醇磷酸酯和生物大分子之间的构效关系，并用于研究新发现的肌醇磷酸酯的生物学功能。因此，非常需要系统且容易获得肌醇立体异构体。由于其生物活性及其在制备其他生物活性分子中的合成效用，因此，实用和方便的合成方法是重要的。我们在此报告了从肌醇中高对映体纯度的所有可能的conduritol非对映异构体和8种肌醇立体异构体的各种衍生物的合成，
• A concise synthetic route to the conduritols from pentoses
  作者：Lise Keinicke、Robert Madsen

  DOI：10.1039/b512009h

  日期：——

  A short synthetic strategy for preparation of the conduritols is described. The key step employs a zinc-mediated fragmentation of protected methyl 5-deoxy-5-iodo-d-pentofuranosides followed by an allylation of the intermediate aldehyde in the same pot. The allylation is performed with 3-bromopropenyl benzoate and occurs with good diastereoselectivity. An amino group can be introduced in the product

  描述了制备conduritols的简短合成策略。关键步骤是使用锌介导的受保护的5-脱氧-5-碘-d-戊呋喃糖苷甲基片段化，然后在同一罐中将中间醛进行烯丙基化。烯丙基化用3-溴丙烯基苯甲酸酯进行，并且以良好的非对映选择性发生。可以通过在烯丙基化之前捕获中间醛作为亚胺来将氨基引入产物中。如此获得的官能化的1，7-辛二烯通过闭环烯烃复分解反应转化成受保护的硬脂醇。
• Enantiospecific synthesis of (4S,5S,6S)-4,5,6-trihydroxycyclohex-2-enone and (+)-conduritol C from fluorobenzene via microbial oxidation
  作者：Howard A. J. Carless、Ozer Z. Oak

  DOI：10.1039/c39910000061

  日期：——

  Epoxidation of the chiral diene 5, produced by Pseudomonas putida oxidation of fluorobenzene, gave fluoroconduritol 9 and cyclohexenone 11; the latter was used in a short synthesis of (+)-conduritol C 1.

  由恶臭假单胞菌氧化氟苯产生的手性二烯5的环氧化，得到氟conduritol 9和环己烯酮11。后者被用于（+）-conduritol C 1的短合成中。
• Enzymatic desymmetrisation of conduritol D. preparation of homochiral intermediates for the synthesis of cyclitols and aminocyclitols
  作者：Angela Patti、Claudia Sanfilippo、Mario Piattelli、Giovanni Nicolosi

  DOI：10.1016/0957-4166(96)00342-4

  日期：1996.9

  From meso-conduritol D tetraacetate four homochiral partial derivatives, namely (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene, (-)-(1R,2R, 3S,4S)-2-hydroxy-1,3 ,4-triacetoxy-5-cyclohexene, (-)-(1R,2R, 3S,4S)-1-benzoyloxy-3,4-diacetoxy-2-hydroxy-5-cyclohexene and (+)-(1R,2R,3S,4S)-3,4-diacetoxy-1,2-dihydroxy-5-cyclohexene, have been prepared through enzymatic reactions catalysed by one of the following lipases: from porcine pancreas, from Mucor miehei and from Candida cylindracea. These compounds are of potential utility in the synthesis of cyclitols and aminocyclitols. As an example, the preparation of the previously unreported (+)-conduramine C-4 is also reported. Copyright (C) 1996 Elsevier Science Ltd