3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2S,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester | 536739-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2S,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester
• CAS: 536739-86-3
• 化学式: C₃₈H₄₈O₁₀
• 分子量: 664.793
• InChiKey: WOMMJOHMWPGSDI-XGIJQDMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  48.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2S,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 lead(II) chloride 四甲基乙二胺 、 硼烷 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 (2S,3S,4R,5R,6R)-2-[2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
  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：

  (3S,4R,5R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2S,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl 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