(2S,3R,4S,5S,6S)-6-Methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-carbaldehyde | 284680-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6S)-6-Methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-carbaldehyde
• CAS: 284680-79-1
• 化学式: C₁₆H₃₆O₆Si₃
• 分子量: 408.715
• InChiKey: PNTQPBDMFQKMSZ-OWYFMNJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6S)-6-Methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-carbaldehyde 在 Amberlyst-15 acidic resin 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 methyl (2E)-3-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]prop-2-enoate
  参考文献：
  名称：

  一锅戴斯马丁过碘烷介导的三甲基甲硅烷基保护的吡喃糖苷和吡喃糖的氧化脱保护和烯化

  摘要：

  碳水化合物的选择性功能化提供了一种引入结构复杂性的强大方法，从而获得具有独特药物特征的独特药物支架。在此，我们描述了使用一锅戴斯-马丁过碘烷介导的氧化脱保护，在C -6处多种常见的三甲基甲硅烷基保护的吡喃糖苷和吡喃糖的有效且选择性的碳-碳键形成反应。随后添加稳定化和非稳定化叶立德以产生良好至中等产率的链烯酸酯碳水化合物和相关类似物。我们还报道了使用酸性树脂介导的乙醇分解以接近定量的产率快速脱除剩余的三甲基甲硅烷基醚基团。

  DOI：

  10.1016/j.carres.2023.108904
• 作为产物：
  描述：

  methyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-α-D-mannopyranoside 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,4S,5S,6S)-6-Methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  一锅戴斯马丁过碘烷介导的三甲基甲硅烷基保护的吡喃糖苷和吡喃糖的氧化脱保护和烯化

  摘要：

  碳水化合物的选择性功能化提供了一种引入结构复杂性的强大方法，从而获得具有独特药物特征的独特药物支架。在此，我们描述了使用一锅戴斯-马丁过碘烷介导的氧化脱保护，在C -6处多种常见的三甲基甲硅烷基保护的吡喃糖苷和吡喃糖的有效且选择性的碳-碳键形成反应。随后添加稳定化和非稳定化叶立德以产生良好至中等产率的链烯酸酯碳水化合物和相关类似物。我们还报道了使用酸性树脂介导的乙醇分解以接近定量的产率快速脱除剩余的三甲基甲硅烷基醚基团。

  DOI：

  10.1016/j.carres.2023.108904

文献信息

• Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker
  作者：Audrey Jeanjean、Marcel Garcia、Alain Leydet、Jean-Louis Montero、Alain Morère

  DOI：10.1016/j.bmc.2006.01.024

  日期：2006.5

  The mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R) is involved in multiple physiological pathways including targeting of lysosomal enzymes, degradation of IGF2, and cicatrization through TGF beta activation. To target potential therapeutics to this membrane receptor, four carboxylate analogues of mannose 6-phosphate (M6P) were synthesized. Three of them, two isosteric carboxylate analogues and a malonate derivative, showed a binding affinity for the M6P/IGF2R equivalent to or higher than that of M6P. Contrary to M6P, all these analogues were particularly stable in human serum. Moreover, these derivatives did not present any cytotoxic activity against two human cell lines. These analogues represent a new potential for the lysosomal targeting of enzyme replacement therapy in lysosomal diseases or to prevent the membrane-associated activities of the M6P/IGF2R. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of new sulfonate and phosphonate derivatives for cation-independent mannose 6-phosphate receptor targeting
  作者：Audrey Jeanjean、Magali Gary-Bobo、Philippe Nirdé、Simon Leiris、Marcel Garcia、Alain Morère

  DOI：10.1016/j.bmcl.2008.09.101

  日期：2008.12

  The cation-independent mannose 6-phosphate receptor (CI-M6PR) is essential for the endocytosis of proteins bearing the mannose 6-phosphate (M6P) recognition marker. This study described the synthesis of M6P and M6S analogs presenting greater affinity for CI-M6PR than their natural compounds. Moreover, the finding of their lack of cytotoxicity for human cells and of their increased stability in human serum supports the high potential of these isosteric derivatives in therapies requiring CI-M6PR targeting. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of new mannose 6-phosphate analogues
  作者：Sébastien Vidal、Marcel Garcia、Jean-Louis Montero、Alain Morère

  DOI：10.1016/s0968-0896(02)00264-x

  日期：2002.12

  Three new analogues of mannose 6-phosphate (M6P)-a sulphate and two carboxylates-have been synthesized and their affinity toward the M6P/IGFII receptor evaluated by affinity column chromatography. These compounds display strong binding to the receptor and therefore are new M6P analogues which may find some dermatological applications. for example healing of post-surgical scars. (C) 2002 Elsevier Science Ltd. All rights reserved.