ethyl 2,4-di-O-benzoyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside | 911040-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4-di-O-benzoyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-5-benzoyloxy-6-ethylsulfanyl-2-methyl-4-(4-oxopentanoyloxy)oxan-3-yl] benzoate
• CAS: 911040-14-7
• 化学式: C₂₇H₃₀O₈S
• 分子量: 514.596
• InChiKey: RTOZVRDBGAYXLN-CTXBDAIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,4-di-O-benzoyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium hydride 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2,4-di-O-benzoyl-3-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-L-rhamnopyranosyl N-phenyl-trifluoroacetimidate
  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 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 、 乙酰丙酸 在 4-二甲氨基吡啶 、 碳酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到ethyl 2,4-di-O-benzoyl-3-O-levulinoyl-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

文献信息

• Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria
  作者：Emiliano Bedini、Antonella Carabellese、Daniela Comegna、Cristina De Castro、Michelangelo Parrilli

  DOI：10.1016/j.tet.2006.06.084

  日期：2006.9

  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.