(2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(allyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl 4-oxopentanoate | 1046465-41-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(allyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl 4-oxopentanoate
• CAS: 1046465-41-1
• 化学式: C₂₃H₂₉NO₈
• 分子量: 447.485
• InChiKey: PWVKKNOAKIQRCP-RMVQUMDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(allyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl 4-oxopentanoate 在 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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：

  乙酰丙酸 、 allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以83%的产率得到(2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(allyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl 4-oxopentanoate
  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