(1R,2S,3S,4R)-1,2,3,4,tetrahydroxy-5-cyclohexene | 80338-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S,4R)-1,2,3,4,tetrahydroxy-5-cyclohexene
• 英文别名: (1R,2S,3S,4R)-5-cyclohexene-1,2,3,4-tetrol；(-)-Conduritol B；L-Condurit B；3r,4t,5c,6t-Tetrahydroxy-cyclohex-1-en；Conduritol-B；(1R,2S,3S,4R)-cyclohex-5-ene-1,2,3,4-tetrol
• CAS: 80338-90-5
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: LRUBQXAKGXQBHA-ZXXMMSQZSA-N

物化性质

• 沸点：
  281.9±40.0 °C(Predicted)
• 密度：
  1.666±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (1R,2S,3S,4R)-1,2,3,4,tetrahydroxy-5-cyclohexene 生成 (-)-Conduritol C tetraacetate
  参考文献：
  名称：

  LE, DRIAN CLAUDE;VIEIRA, ERIC;VOGEL, PIERRE, HELV. CHIM. ACTA., 72,(1989) N, C. 338-347

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以100%的产率得到(1R,2S,3S,4R)-1,2,3,4,tetrahydroxy-5-cyclohexene
  参考文献：
  名称：

  Enzymatic resolution of (±)-conduritol-B, a key intermediate for the synthesis of glycosidase inhibitors

  摘要：

  Lipases from porcine pancreas, Candida cylindracea and Mucor miehei (adsorbed on support, Lipozyme(R) IM) catalysed in t-butylmethylether the alcoholysis of rac-conduritol-B peracetate, (+/-)-1, by n-butanol to give enantiopure (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene, (-)-3, and (1S,2R,3R,4S)-tetraacetoxy-cyclohex-5-ene, (+)-1. The enantioforms (+)- and (-)-conduritol-B, obtained after chemical hydrolysis of (-)-3 and (+)-1, respectively, may be employed to prepare both the enantiomers of conduritol-B epoxide and cyclophellitol, powerful inhibitors of glycosidases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00344-4

文献信息

• 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，
• Total Syntheses of (?)-Conduritol B ((?)-1L-Cyclohex-5-ene-1,3/2,4-tetrol) and of (+)-Conduritol F((+)-1D-Cyclohex-5-ene-1,2,4/3-tetrol). Determination of the Absolute Configuration of (+)-Leucanthemito
  作者：Claude Le Drian、Jean-Paul Vionnet、Pierre Vogel

  DOI：10.1002/hlca.19900730118

  日期：1990.1.31

  The ‘naked sugar’ (+)-(1R,2R4R)-2-endo-cyano-7-oxabicyclo[2.2.1]hept-5-sn-2-exo-yl acetate ((+)-4) was converted (7 steps, 45% overall) with high stereoselectivity into (−)-(4R,5S,6R)-4,5,6-tris[(tert-butyl)dimethylsilyl]oxy}cyclohex-2-en-1-one ((−)-11). Reduction of (−)-1 with NaBH4- CeCl3 · 7 H2O, followed by deprotection of the silyl ether moieties gave (+)-conduritol F ((+)-1; 47%) whose characteristics

  '裸糖'（+）-（1 R，2 R 4 R）-2-内-氰基-7-氧杂双环[2.2.1]庚-5-sn-2-乙酸乙酸外酯（（+）- 4）（具有7个步骤，总产率为45％）以高立体选择性转化为（-）-（4 R，5 S，6 R）-4,5,6-tris [（（叔丁基）二甲基甲硅烷基]氧基}环己基-2-en-1-one（（-）- 11）。用NaBH 4 -CeCl 3 ·7 H 2 O还原（-）- 1，然后将甲硅烷基醚部分脱保护，得到（+）-硬脂醇F（（+）- 1; 47％）的特性与天然（+）-亮氨酸-苏糖醇的特性相同。用DIBAH还原（-）- 11，然后使甲硅烷基醚部分脱保护，得到（-）-conduritol B（（-）- 3 ; 51％）。
• Paulsen, Hans; Roeben, Wolfgang; Heiker, Fred R., Chemische Berichte, 1981, vol. 114, # 10, p. 3242 - 3252
  作者：Paulsen, Hans、Roeben, Wolfgang、Heiker, Fred R.

  DOI：——

  日期：——
• Facile Synthetic Routes to All Possible Enantiomeric Pairs of Conduritol Stereoisomers via Efficient Enzymatic Resolution of Conduritol B and C Derivatives
  作者：Yong-Uk Kwon、Sung-Kee Chung

  DOI：10.1021/ol0164233

  日期：2001.9.1

  The first synthesis of all possible enantiomeric pairs of conduritol stereoisomers has been accomplished by efficient enzymatic resolution of conduritol B and C derivatives, followed by oxidation/reduction and the Mitsunobu reaction in stereo- and regioselective manners. Reaction: see text.
• LE, DRIAN CLAUDE;VIEIRA, ERIC;VOGEL, PIERRE, HELV. CHIM. ACTA., 72,(1989) N, C. 338-347
  作者：LE, DRIAN CLAUDE、VIEIRA, ERIC、VOGEL, PIERRE

  DOI：——

  日期：——