allyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside | 911039-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: Bz(-2)[Bz(-4)]Rha(a1-3)[Bz(-2)][Bz(-4)]Rha(a1-2)[Bz(-3)][Bz(-4)]Rha(a1-2)[Bz(-3)][Bz(-4)]Rha(a)-O-allyl；[(2S,3R,4R,5R,6S)-5-benzoyloxy-6-[(2S,3R,4R,5S,6S)-3,5-dibenzoyloxy-2-[(2S,3R,4R,5S,6S)-4,5-dibenzoyloxy-2-[(2R,3R,4R,5S,6S)-4,5-dibenzoyloxy-6-methyl-2-prop-2-enoxyoxan-3-yl]oxy-6-methyloxan-3-yl]oxy-6-methyloxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] benzoate
• CAS: 911039-97-9
• 化学式: C₈₃H₇₈O₂₅
• 分子量: 1475.52
• InChiKey: JESCKCPQDBKBMT-SWIWRODVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  108
• 可旋转键数：
  33
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  305
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  (3,4-di-O-benzoyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-L-rhamnopyranosyl N-phenyltrifluoroacetimidate 、 allyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria

  摘要：

  The synthesis of the tetrasaccharide rhamnanic motif alpha-L-Rha-(1 -> 3)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl ttifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.084
• 作为产物：
  描述：

  allyl (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 硫脲 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以71%的产率得到allyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria

  摘要：

  The synthesis of the tetrasaccharide rhamnanic motif alpha-L-Rha-(1 -> 3)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl ttifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.084