Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester | 625108-33-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester
• CAS: 625108-33-0
• 化学式: C₃₃H₄₁N₃O₁₇
• 分子量: 751.698
• InChiKey: VJOYNSUVVJEZEU-BBFVIDQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  260.55
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester 在 palladium on activated charcoal 氢气 、 magnesium methanolate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-((1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentahydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Synthesis of 1-d- and 1-l-myo-inosityl 2-N-acetamido-2-deoxy-α-d-glucopyranoside establishes substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase

  摘要：

  Mycothiol (MSH, 1-D-myo-inosityl 2-(N-acetyl-L-cysteinyl)amido-2-deoxy-alpha-D-glucopyrano side) is the principal low molecular weight thiol in actinomycetes. The enzyme 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase (AcGI deacetylase) is involved in the biosynthesis of MSH and forms the free amine 1-D-niyo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside, which is used in the third of four steps of MSH biosynthesis. Here, we report the synthesis of two isomers of AcGL which contain either 1-L-myo-inositol or 1-D-myo-inositol. These synthetic products were used to investigate substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00154-8
• 作为产物：
  描述：

  (+/-)-4-O-benzyl-1,2:5,6-di-O-cyclohexylidene-myo-inositol 在 2,6-diisopropyl-4-methylpyridine 、 silver trifluoromethanesulfonate 、 乙二醇 、 (+)-10-camphorsulfonic acid 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 Acetic acid (1R,2R,3R,4S,5R,6R)-2,3,4-triacetoxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester
  参考文献：
  名称：

  Synthesis of 1-d- and 1-l-myo-inosityl 2-N-acetamido-2-deoxy-α-d-glucopyranoside establishes substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase

  摘要：

  Mycothiol (MSH, 1-D-myo-inosityl 2-(N-acetyl-L-cysteinyl)amido-2-deoxy-alpha-D-glucopyrano side) is the principal low molecular weight thiol in actinomycetes. The enzyme 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase (AcGI deacetylase) is involved in the biosynthesis of MSH and forms the free amine 1-D-niyo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside, which is used in the third of four steps of MSH biosynthesis. Here, we report the synthesis of two isomers of AcGL which contain either 1-L-myo-inositol or 1-D-myo-inositol. These synthetic products were used to investigate substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00154-8