S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside | 407616-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8S,8aR)-7,8-bis[(4-bromophenyl)methoxy]-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 407616-83-5
• 化学式: C₃₃H₃₀Br₂O₅S
• 分子量: 698.472
• InChiKey: ULQKXDFAEBOODS-HOEDGPACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) 三氟甲磺酸酐 、 3 A molecular sieve 、 potassium tert-butylate 、 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 、 甲苯 为溶剂， 反应 9.25h， 生成 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-O-benzylidene-2,3-di-O-p-(N-methyl-N-phenylamino)benzyl-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：

  对溴溴苄 、 phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以100%的产率得到S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-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

• 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.