1-O-(4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol | 407616-92-6

• 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: 1-O-(4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol
• CAS: 407616-92-6
• 化学式: C₄₆H₈₄O₁₃Si
• 分子量: 873.251
• InChiKey: ZTPCGALUSJMWPD-OTQWOAMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.04
• 重原子数：
  60.0
• 可旋转键数：
  30.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  151.35
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-O-(4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol 在 三氟化硼乙醚 、 苯硫酚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以85%的产率得到1-O-(4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-D-erythritol
  参考文献：
  名称：

  Synthesis of the mannosyl erythritol lipid MEL A; confirmation of the configuration of the meso-erythritol moiety

  摘要：

  The total synthesis of the two possible diastereomers of mannosylerythritol lipid A, a novel biosurfactant from Candida antartica T-34 with promising anti-proliferative properties in several cell lines, is described. By comparison with an authentic sample, the natural material is confirmed as a single diastereomer with the 4-O-(beta -D-mannopyranosyl) D-erythritol configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01087-0
• 作为产物：
  描述：

  1-O-(4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 1-O-(4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol
  参考文献：
  名称：

  Synthesis of the mannosyl erythritol lipid MEL A; confirmation of the configuration of the meso-erythritol moiety

  摘要：

  The total synthesis of the two possible diastereomers of mannosylerythritol lipid A, a novel biosurfactant from Candida antartica T-34 with promising anti-proliferative properties in several cell lines, is described. By comparison with an authentic sample, the natural material is confirmed as a single diastereomer with the 4-O-(beta -D-mannopyranosyl) D-erythritol configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01087-0