(2S,3R,4R,5S,6S)-4-(benzyloxy)-6-methyl-5-(naphthalen-2-ylmethoxy)-2-(phenylthio)tetrahydro-2H-pyran-3-yl pivalate | 1046465-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6S)-4-(benzyloxy)-6-methyl-5-(naphthalen-2-ylmethoxy)-2-(phenylthio)tetrahydro-2H-pyran-3-yl pivalate
• CAS: 1046465-38-6
• 化学式: C₃₅H₃₈O₅S
• 分子量: 570.75
• InChiKey: QRMWVNZUJVMYAP-CGHDKJPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-4,6-di-O-benzoyl-α-D-glucopyranoside 、 (2S,3R,4R,5S,6S)-4-(benzyloxy)-6-methyl-5-(naphthalen-2-ylmethoxy)-2-(phenylthio)tetrahydro-2H-pyran-3-yl pivalate 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%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：

  phenyl 3-O-benzyl-2-O-pivaloyl-1-thio-α-L-rhamnopyranose 、 2-溴甲基萘 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到(2S,3R,4R,5S,6S)-4-(benzyloxy)-6-methyl-5-(naphthalen-2-ylmethoxy)-2-(phenylthio)tetrahydro-2H-pyran-3-yl pivalate
  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