(2R)-4-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butane-1,2-diol | 536739-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-4-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butane-1,2-diol
• CAS: 536739-98-7
• 化学式: C₃₈H₄₄O₇
• 分子量: 612.763
• InChiKey: AOQUTUYFRZIONE-GEPCBSDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-4-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butane-1,2-diol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 33.0h， 生成 [(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：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 lead(II) chloride 4-二甲氨基吡啶 、 四甲基乙二胺 、 硼烷 、 四氯化钛 、 sodium hydride 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.17h， 生成 (2R)-4-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butane-1,2-diol
  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

文献信息

• Synthesis of Some Biologically Relevant β-<i>C</i>-Glycoconjugates
  作者：Maarten H. D. Postema、Jared L. Piper

  DOI：10.1021/ol034363q

  日期：2003.5.1

  [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.