3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester | 845884-21-1

• 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-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester
• 英文别名: [(2R,3R,4R)-1,3,4-tris[(4-methoxyphenyl)methoxy]hex-5-en-2-yl] 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 845884-21-1
• 化学式: C₃₈H₄₈O₁₀
• 分子量: 664.793
• InChiKey: WOMMJOHMWPGSDI-ADFXPUFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester 在 lead(II) chloride RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 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， 反应 4.0h， 生成 (2R,3R,4R)-6-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-3,4-dihydro-2H-pyran
  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：

  2,3,5-tri-O-(4-methoxybenzyl)-4-O-formyl-D-lyxose 在 4-二甲氨基吡啶 、 sodium methylate 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 19.27h， 生成 3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propionic acid (1R,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyl ester
  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

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.