2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol | 407616-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol
• CAS: 407616-81-3
• 化学式: C₁₂H₂₆O₄Si
• 分子量: 262.422
• InChiKey: YMTJEKHJTJBPRN-OUAUKWLOSA-N

物化性质

• 沸点：
  298.4±35.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 三氟甲磺酸酐 吡啶 、 4-二甲氨基吡啶 、 1-(苯基亚硫酰基)哌啶 、 3 A molecular sieve 、 水 、 氢气 、 mercury dichloride 、 mercury(II) oxide 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 31.08h， 生成 1-O-(4,6-O-benzylidene-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
• 作为产物：
  描述：

  (2R,4R,5R)-5-羟基-2-甲基-1,3-二恶烷-4-甲醛 在 咪唑 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 水 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.5h， 生成 2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-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

文献信息

• Method of forming glycosidic bonds from thioglycosides using an N,N-dialkylsulfinamide
  申请人：——

  公开号：US20040019198A1

  公开（公告）日：2004-01-29

  A method of forming a glycosidic bond utilizing an activated thioglycoside is disclosed. The thioglycoside is activated by an N,N-dialkylsulfinamide and trifluoromethanesulfonic anhydride. The method allows the facile synthesis of disaccharides, oligosacchraides, and polysaccharides in solution or on a polymer support.

  揭示了一种利用活化硫代糖苷键的方法。该硫代糖苷经N,N-二烷基亚磺酰胺和三氟甲磺酸酐激活。该方法允许在溶液中或在聚合物支撑上轻松合成二糖、寡糖和多糖。
• 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.