Phenyl 2,3-di-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside | 819798-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Phenyl 2,3-di-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside
• 英文别名: Phenyl 2,3-di-O-benzyl-6-O-trityl-1-thio-beta-D-glucopyranoside；(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-6-phenylsulfanyl-2-(trityloxymethyl)oxan-3-ol
• CAS: 819798-53-3
• 化学式: C₄₅H₄₂O₅S
• 分子量: 694.891
• InChiKey: CFPLPAWTSRKMTN-IYFSMEFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Phenyl 2,3-di-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside 在 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 2,3-Di-O-benzyl-4-O-n-octyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Structure–Activity Relationships for Antibacterial to Antifungal Conversion of Kanamycin to Amphiphilic Analogues

  摘要：

  Novel fungicides are urgently needed. It was recently reported that the attachment of an octyl group at the O-4 '' position of kanamycin B converts this antibacterial aminoglycoside into a novel antifungal agent. To elucidate the structure-activity relationship (SAR) for this phenomenon, a lead compound FG03 with a hydroxyl group replacing the 3 ''-NH2 group of kanamycin B was synthesized. FG03's antifungal activity and Synthetic scheme inspired the synthesis of a library of kanamycin B analogues alkylated at various hydroxyl groups. SAR. studies of the library revealed that for antifungal activity the O-4 '' position is the optimal site for attaching a linear alkyl chain and that the 3 ''-NH2 and 6 ''-OH groups of the kanamycin B parent molecule are not essential for antifungal activity. The discovery of lead compound, FG03, is an example of reviving clinically obsolete drugs like kanamycin by simple chemical modification and an alternative strategy for discovering novel antimicrobials.

  DOI：

  10.1021/acs.joc.5b00248
• 作为产物：
  描述：

  三苯基氯甲烷 、 phenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 12.0h， 以72%的产率得到Phenyl 2,3-di-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  METHOD OF SYNTHESIZING SUGAR CHAIN

  摘要：

  本发明的目的是提供一种有效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性示例。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，其特征在于根据已确定的反应系统中副反应减少的指标，改变糖链合成反应系统中的温度上升速率。

  公开号：

  EP1640379A1

文献信息

• Method for synthesizing sugar chain(s)
  申请人：Kanie Osamu

  公开号：US20060166278A1

  公开（公告）日：2006-07-27

  An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a method of solid-phase synthesis of sugar chain(s) for synthesizing multiple types of sugar chains in at least one sugar chain synthesis reaction system comprising multiple types of monosaccharide units, which is characterized in that it comprises changing the temperature in the sugar chain synthesis reaction system depending on the temperature rising rate that has been determined based on a decrease in side reaction(s) in the reaction system as an indicator.

  本发明的目的是提供一种高效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性分子。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，该反应系统包含多种单糖单元，其特征在于根据反应系统中副反应的减少作为指标确定的温度升高速率来改变糖链合成反应系统中的温度。
• Selective Oxidation of Glycosyl Sulfides to Sulfoxides with Sodium Hypochlorite and Catalyzed by Metalloporphyrins
  作者：Jian-Ying Huang、Shi-Jun Li、Yan-Guang Wang

  DOI：10.1080/07328303.2010.483041

  日期：2010.4

  An efficient and selective method for oxidation of glycosyl sulfides to the corresponding glycosyl sulfoxides with metalloporphyrins as catalysts and sodium hypochlorite as oxidant was achieved under mild conditions. High chemoselectivity and diastereomeric excesses were obtained. Both acid-labile protected groups and carbon-carbon double bonds of allyl groups tolerated under these conditions.
• METHOD OF SYNTHESIZING SUGAR CHAIN
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1640379A1

  公开（公告）日：2006-03-29

  An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a method of solid-phase synthesis of sugar chain(s) for synthesizing multiple types of sugar chains in at least one sugar chain synthesis reaction system comprising multiple types of monosaccharide units, which is characterized in that it comprises changing the temperature in the sugar chain synthesis reaction system depending on the temperature rising rate that has been determined based on a decrease in side reaction(s) in the reaction system as an indicator.

  本发明的目的是提供一种有效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性示例。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，其特征在于根据已确定的反应系统中副反应减少的指标，改变糖链合成反应系统中的温度上升速率。
• Structure–Activity Relationships for Antibacterial to Antifungal Conversion of Kanamycin to Amphiphilic Analogues
  作者：Marina Fosso、Madher N. AlFindee、Qian Zhang、Vincent de Paul Nzuwah Nziko、Yukie Kawasaki、Sanjib K. Shrestha、Jeremiah Bearss、Rylee Gregory、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1021/acs.joc.5b00248

  日期：2015.5.1

  Novel fungicides are urgently needed. It was recently reported that the attachment of an octyl group at the O-4 '' position of kanamycin B converts this antibacterial aminoglycoside into a novel antifungal agent. To elucidate the structure-activity relationship (SAR) for this phenomenon, a lead compound FG03 with a hydroxyl group replacing the 3 ''-NH2 group of kanamycin B was synthesized. FG03's antifungal activity and Synthetic scheme inspired the synthesis of a library of kanamycin B analogues alkylated at various hydroxyl groups. SAR. studies of the library revealed that for antifungal activity the O-4 '' position is the optimal site for attaching a linear alkyl chain and that the 3 ''-NH2 and 6 ''-OH groups of the kanamycin B parent molecule are not essential for antifungal activity. The discovery of lead compound, FG03, is an example of reviving clinically obsolete drugs like kanamycin by simple chemical modification and an alternative strategy for discovering novel antimicrobials.