Octadecanoic acid (R)-1-octadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester | 536739-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Octadecanoic acid (R)-1-octadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester
• CAS: 536739-96-5
• 化学式: C₇₄H₁₁₂O₉
• 分子量: 1145.7
• InChiKey: HTKFPBBODQTQPB-MYVHDYCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.48
• 重原子数：
  83.0
• 可旋转键数：
  51.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Octadecanoic acid (R)-1-octadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 15.0h， 以88%的产率得到[(2R)-2-octadecanoyloxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butyl] octadecanoate
  参考文献：
  名称：

  Synthesis of Some Biologically Relevant β-C-Glycoconjugates

  摘要：

  [GRAPHICS]An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.

  DOI：

  10.1021/ol034363q
• 作为产物：
  描述：

  (2S,3S,4R,5R,6R)-2-[2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol 在 4-二甲氨基吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 Octadecanoic acid (R)-1-octadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester
  参考文献：
  名称：

  Synthesis of Some Biologically Relevant β-C-Glycoconjugates

  摘要：

  [GRAPHICS]An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.

  DOI：

  10.1021/ol034363q