octyl 2,3-di-O-benzoyl-5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside | 569659-41-2

• 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: octyl 2,3-di-O-benzoyl-5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
• CAS: 569659-41-2
• 化学式: C₆₂H₆₈O₁₃Si
• 分子量: 1049.3
• InChiKey: AGVVLTZCOCOSPL-DNKHUJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.31
• 重原子数：
  76.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  octyl 2,3-di-O-benzoyl-5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 n-Bu₄F*3H₂O 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 octyl 2,3-di-O-benzoyl-5-O-(2,3-di-O-benzoyl-α-D-arabinofuranosyl)-(5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl))-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of octyl arabinofuranosides as substrates for mycobacterial arabinosyltransferases

  摘要：

  A panel of octyl oligosaccharides comprised of arabinofuranose rings have been synthesized via efficient and readily scaleable routes. The key glycosylation reactions involved the coupling of octyl glycoside acceptors with the appropriate thioglycosides using N-iodosuccinimide and silver triflate activation. These syntheses were undertaken to provide substrates suitable for use in assays of mycobacterial arabinosyltransferases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00541-4
• 作为产物：
  描述：

  p-cresyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside 、 octyl 2,3-di-O-benzoyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到octyl 2,3-di-O-benzoyl-5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of octyl arabinofuranosides as substrates for mycobacterial arabinosyltransferases

  摘要：

  A panel of octyl oligosaccharides comprised of arabinofuranose rings have been synthesized via efficient and readily scaleable routes. The key glycosylation reactions involved the coupling of octyl glycoside acceptors with the appropriate thioglycosides using N-iodosuccinimide and silver triflate activation. These syntheses were undertaken to provide substrates suitable for use in assays of mycobacterial arabinosyltransferases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00541-4