3,4,6-tri-O-benzyl-1,2-dideoxy-5-O-[(2-methoxyphenyl)acetyl]-D-arabinohex-1-enitol | 536739-77-2

• 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: 3,4,6-tri-O-benzyl-1,2-dideoxy-5-O-[(2-methoxyphenyl)acetyl]-D-arabinohex-1-enitol
• 英文别名: 3,4,6-tri-O-benzyl-1,2-dideoxy-5-O-(2'-methoxyphenylacetyl)-D-arabinohex-1-enitol；[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl] 2-(2-methoxyphenyl)acetate
• CAS: 536739-77-2
• 化学式: C₃₆H₃₈O₆
• 分子量: 566.694
• InChiKey: WIHYZNCCUZZNSK-QEQHASERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,2-dideoxy-5-O-[(2-methoxyphenyl)acetyl]-D-arabinohex-1-enitol 在 lead(II) chloride RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 硼烷四氢呋喃络合物 、 四甲基乙二胺 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 1'-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-methoxytoluene
  参考文献：
  名称：

  RCM-Based Synthesis of a Variety of β-C-Glycosides and Their in Vitro Anti-Solid Tumor Activity

  摘要：

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo040254t
• 作为产物：
  描述：

  2-甲氧基苯乙酸 、 (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以89%的产率得到3,4,6-tri-O-benzyl-1,2-dideoxy-5-O-[(2-methoxyphenyl)acetyl]-D-arabinohex-1-enitol
  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

• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.
• 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.