4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranoside | 407616-97-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranoside
• 英文别名: [(2R,4aR,6R,7S,8S,8aR)-6-[(Z)-4-[tert-butyl(diphenyl)silyl]oxybut-2-enoxy]-7-dodecanoyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] dodecanoate
• CAS: 407616-97-1
• 化学式: C₅₇H₈₄O₉Si
• 分子量: 941.374
• InChiKey: OPFPBIKOSRWYSC-QUPZUQRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.64
• 重原子数：
  67
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranoside 在 吡啶 、 碘 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside
  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：

  phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 3 A molecular sieve 、 potassium tert-butylate 、 四氯化锡 、 sodium hydride 、 间氯过氧苯甲酸 、 2-(二叔丁基膦)联苯 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.75h， 生成 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranoside
  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

文献信息

• Synthesis of the mannosyl erythritol lipid MEL A; confirmation of the configuration of the meso-erythritol moiety
  作者：David Crich、Marco A de la Mora、Raymundo Cruz

  DOI：10.1016/s0040-4020(01)01087-0

  日期：2002.1

  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.