| 1046465-65-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 1046465-65-9
• 化学式: C₇₃H₆₂O₁₈
• 分子量: 1227.28
• InChiKey: RQEBNWIVTQTCOT-JIJKKBEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.45
• 重原子数：
  91.0
• 可旋转键数：
  26.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  224.18
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到
  参考文献：
  名称：

  Synthesis of a tetrasaccharide phosphate from the linkage region of the arabinogalactan–peptidoglycan complex in the mycobacterial cell wall

  摘要：

  The synthesis of dibenzyl 6-O-naphthylmethyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 -> 5)-2,3-di-O-benzoyl-6-O-benzyl- beta-D-galactofuranosyl-(1 -> 4)-3-O-benzyl-2-O-pivaloyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-4,6-di-O-benzoyl-alpha-glucopyranosyl phosphate (1), a protected form of the tetrasaccharide phosphate of the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall, has been accomplished. Key steps include the coupling of four monosaccharide building blocks with complete stereoselectivity by glycosylations employing thioglycosides, 2'-carboxybenzyl glycosides, and glycosyl fluorides as glycosyl donors. The alpha-glycosyl phosphate linkage was also stereoselectively elaborated by reaction of a tetrasaccharide hermacetal with tetrabenzyl pyrophosphate in the presence of a base. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.009
• 作为产物：
  描述：

  在 palladium dihydroxide 乙酸铵 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 以89%的产率得到
  参考文献：
  名称：

  Synthesis of a tetrasaccharide phosphate from the linkage region of the arabinogalactan–peptidoglycan complex in the mycobacterial cell wall

  摘要：

  The synthesis of dibenzyl 6-O-naphthylmethyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 -> 5)-2,3-di-O-benzoyl-6-O-benzyl- beta-D-galactofuranosyl-(1 -> 4)-3-O-benzyl-2-O-pivaloyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-4,6-di-O-benzoyl-alpha-glucopyranosyl phosphate (1), a protected form of the tetrasaccharide phosphate of the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall, has been accomplished. Key steps include the coupling of four monosaccharide building blocks with complete stereoselectivity by glycosylations employing thioglycosides, 2'-carboxybenzyl glycosides, and glycosyl fluorides as glycosyl donors. The alpha-glycosyl phosphate linkage was also stereoselectively elaborated by reaction of a tetrasaccharide hermacetal with tetrabenzyl pyrophosphate in the presence of a base. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.009