3-chloro-D-3-deoxy-glucose | 4991-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-D-3-deoxy-glucose
• 英文别名: 3-chloro-ξ-D-3-deoxy-glucopyranose；3-Chloro-3-deoxy-D-glucopyranose；(3S,4S,5R,6R)-4-chloro-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 4991-01-9
• 化学式: C₆H₁₁ClO₅
• 分子量: 198.603
• InChiKey: CRJLKIILIKSPDH-CBPJZXOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chloro-D-3-deoxy-glucose 在 吡啶 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氢溴酸 、 三正丁基氢锡 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 42.0h， 生成 1,2,4,6-tetra-O-acetyl-3-deoxy-β-D-ribo-hexoopyranose
  参考文献：
  名称：

  一系列脱氧和脱氧氟-α-d-“吡喃葡萄糖基”磷酸酯的合成和水解

  摘要：

  摘要描述了三种脱氧-α-d-“吡喃葡萄糖基”磷酸酯和一系列双脱氧单氟-和双脱氧二氟-α-d-吡喃葡萄糖基磷酸酯的合成。测定其酸催化水解的速率常数。已显示糖环中的脱氧可将水解速率提高至先前对一系列苯基脱氧d-“吡喃葡萄糖苷”进行酸催化水解所见的程度[Mega and Matsushima，J. Biochem。东京，94（1983）1637]。这表明这两个反应的过渡态基本相同。通过确定一系列脱氧和脱氧氟取代的6-脱氧-6-氟-α-d-葡萄糖基吡喃糖基磷酸酯的水解速率，可证明对糖环的取代基作用具有可预测的加性，并且本质上主要是电子的，

  DOI：

  10.1016/0008-6215(89)80055-2
• 作为产物：
  描述：

  3-氯-3-脱氧-1,2:5,6-二异亚丙基-alpha-d-呋喃葡萄糖 在 Dowex 50W-X8 、 水 作用下， 反应 18.0h， 生成 3-chloro-D-3-deoxy-glucose
  参考文献：
  名称：

  Aldotetroses and C(3)-Modified Aldohexoses as Substrates for N-Acetylneuraminic Acid Aldolase: A Model for the Explanation of the Normal and the Inversed Stereoselectivity

  摘要：

  The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase. C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition. Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions. The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.

  DOI：

  10.1021/jo00117a016

文献信息

• The synthesis and hydrolysis of a series of deoxy- and deoxyfluoro-α-d- “glucopyranosyl” phosphates
  作者：Stephen G. Withers、M.David Percival、Ian P. Street

  DOI：10.1016/0008-6215(89)80055-2

  日期：1989.4

  syntheses of three deoxy-α- d - “glucopyranosyl” phosphates and a series of dideoxymonofluoro- and dideoxydifluoro-α- d -glucopyranosyl phosphates are described. Rate constants for their acid-catalyzed hydrolysis were determined. Deoxygenation in the sugar ring was shown to increase the hydrolysis rate to the extent seen previously for acid-catalyzed hydrolysis of a series of phenyl deoxy- d - “glucopyranosides”

  摘要描述了三种脱氧-α-d-“吡喃葡萄糖基”磷酸酯和一系列双脱氧单氟-和双脱氧二氟-α-d-吡喃葡萄糖基磷酸酯的合成。测定其酸催化水解的速率常数。已显示糖环中的脱氧可将水解速率提高至先前对一系列苯基脱氧d-“吡喃葡萄糖苷”进行酸催化水解所见的程度[Mega and Matsushima，J. Biochem。东京，94（1983）1637]。这表明这两个反应的过渡态基本相同。通过确定一系列脱氧和脱氧氟取代的6-脱氧-6-氟-α-d-葡萄糖基吡喃糖基磷酸酯的水解速率，可证明对糖环的取代基作用具有可预测的加性，并且本质上主要是电子的，
• Aldotetroses and C(3)-Modified Aldohexoses as Substrates for N-Acetylneuraminic Acid Aldolase: A Model for the Explanation of the Normal and the Inversed Stereoselectivity
  作者：Wolfgang Fitz、Jan-Robert Schwark、Chi-Huey Wong

  DOI：10.1021/jo00117a016

  日期：1995.6

  The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase. C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition. Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions. The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.