cyclohexyl 2-(2-chloroacetamido)-2-deoxy-1-thio-α-D-glucopyranoside | 862269-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2-(2-chloroacetamido)-2-deoxy-1-thio-α-D-glucopyranoside
• 英文别名: 2-chloro-N-[(2R,3R,4R,5S,6R)-2-cyclohexylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 862269-23-6
• 化学式: C₁₄H₂₄ClNO₅S
• 分子量: 353.867
• InChiKey: SLXZWROLCLUXIS-DKTYCGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyclohexyl 2-(2-chloroacetamido)-2-deoxy-1-thio-α-D-glucopyranoside 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到cyclohexyl 2-deoxy-2-glycinamido-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  A Family of Mycothiol Analogues

  摘要：

  A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thioglycosides that superficially resemble the enzyme-binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners. To the extent that these analogues mimic the transition states derived from substrates of the mycothiol-associated enzymes, they might prove useful as inhibitors and, ultimately, as drug leads.

  DOI：

  10.1081/car-200059965
• 作为产物：
  描述：

  氯乙酸 、 cyclohexyl 2-amino-2-deoxy-1-thio-α-D-glucopyranoside 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以72%的产率得到cyclohexyl 2-(2-chloroacetamido)-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  A Family of Mycothiol Analogues

  摘要：

  A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thioglycosides that superficially resemble the enzyme-binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners. To the extent that these analogues mimic the transition states derived from substrates of the mycothiol-associated enzymes, they might prove useful as inhibitors and, ultimately, as drug leads.

  DOI：

  10.1081/car-200059965

文献信息

• A Family of Mycothiol Analogues
  作者：Spencer Knapp、Benjamin Amorelli、Etzer Darout、Christian C. Ventocilla、Lawrence M. Goldman、Richard A. Huhn、Ellen C. Minnihan

  DOI：10.1081/car-200059965

  日期：2005.3

  A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thioglycosides that superficially resemble the enzyme-binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners. To the extent that these analogues mimic the transition states derived from substrates of the mycothiol-associated enzymes, they might prove useful as inhibitors and, ultimately, as drug leads.