1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol | 1228173-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol
• CAS: 1228173-37-2
• 化学式: C₂₂H₃₈N₂O₁₄S
• 分子量: 586.615
• InChiKey: QYARBTQXAVWUQB-IVRHHHDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.71
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  264.8
• 氢给体数：
  10.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol 在 三氟乙酸 作用下， 反应 0.33h， 生成
  参考文献：
  名称：

  Desymmetrization of 2,4,5,6-Tetra-O-benzyl-d-myo-inositol for the Synthesis of Mycothiol

  摘要：

  An efficient chemical synthesis of mycothiol Involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated D-myo-inositol as the key step Is described. Together with a highly alpha-stereoselective D-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.

  DOI：

  10.1021/ol202218n
• 作为产物：
  描述：

  1-O-[2-azido-3-O-(4-bromobenzyl)-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol 在 盐酸 、 氢气 、 palladium(II) hydroxide 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol
  参考文献：
  名称：

  Desymmetrization of 2,4,5,6-Tetra-O-benzyl-d-myo-inositol for the Synthesis of Mycothiol

  摘要：

  An efficient chemical synthesis of mycothiol Involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated D-myo-inositol as the key step Is described. Together with a highly alpha-stereoselective D-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.

  DOI：

  10.1021/ol202218n

文献信息

• Mycothiol synthesis by an anomerization reaction through endocyclic cleavage
  作者：Shino Manabe、Yukishige Ito

  DOI：10.3762/bjoc.12.35

  日期：——

  Mycothiol is found in Gram-positive bacteria, where it helps in maintaining a reducing intracellular environment and it plays an important role in protecting the cell from toxic chemicals. The inhibition of the mycothiol biosynthesis is considered as a treatment for tuberculosis. Mycothiol contains an α-aminoglycoside, which is difficult to prepare stereoselectively by a conventional glycosylation reaction. In this study, mycothiol was synthesized by an anomerization reaction from an easily prepared β-aminoglycoside through endocyclic cleavage.

  Mycothiol在革兰氏阳性细菌中发现，它有助于维持还原的细胞内环境，并在保护细胞免受有毒化学物质侵害方面发挥重要作用。抑制mycothiol生物合成被认为是治疗结核病的一种方法。Mycothiol含有α-氨基糖苷，通过传统的糖基化反应难以立体选择性地制备。在这项研究中，通过内环裂解，从易于制备的β-氨基糖苷通过异构化反应合成了mycothiol。
• Intramolecular α-Glucosaminidation: Synthesis of Mycothiol
  作者：Kehinde Ajayi、Vinay V. Thakur、Robert C. Lapo、Spencer Knapp

  DOI：10.1021/ol1008334

  日期：2010.6.4

  A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively alpha-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.