ethyl 3,4-di-O-benzoyl-2-O-chloroacetyl-1-thio-α-L-rhamnopyranoside | 911040-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4-di-O-benzoyl-2-O-chloroacetyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-4-benzoyloxy-5-(2-chloroacetyl)oxy-6-ethylsulfanyl-2-methyloxan-3-yl] benzoate
• CAS: 911040-03-4
• 化学式: C₂₄H₂₅ClO₇S
• 分子量: 492.977
• InChiKey: NYVDWITYOINWAE-YARBZOEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-di-O-benzoyl-2-O-chloroacetyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3,4-di-O-benzoyl-2-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
  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：

  ethyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 ethyl 3,4-di-O-benzoyl-2-O-chloroacetyl-1-thio-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