2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-methylsulfanylmethoxymethyl-tetrahydro-pyran-4-yl ester | 592533-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-methylsulfanylmethoxymethyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6S)-5-acetamido-4-(2,2-dimethylpropanoyloxy)-2-(methylsulfanylmethoxymethyl)-6-phenylmethoxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 592533-36-3
• 化学式: C₂₇H₄₁NO₈S
• 分子量: 539.69
• InChiKey: YNNQHIRHMJYAGN-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-methylsulfanylmethoxymethyl-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 四氮唑 、 氢气 、 双氧水 、 镍 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-acetylamino-5-(2,2-dimethyl-propionyloxy)-6-methoxymethyl-2-phosphonooxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases

  摘要：

  A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-alpha-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00287-7
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 三氟化硼乙醚 、 水 、 过氧化苯甲酰 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.0h， 生成 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-methylsulfanylmethoxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases

  摘要：

  A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-alpha-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00287-7

文献信息

• Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases
  作者：Patricia Busca、Véronique Piller、Friedrich Piller、Olivier R. Martin

  DOI：10.1016/s0960-894x(03)00287-7

  日期：2003.6

  A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-alpha-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity. (C) 2003 Elsevier Science Ltd. All rights reserved.