(2S,3S,4R,5S,6R)-2-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran | 845884-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6R)-2-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran
• CAS: 845884-23-3
• 化学式: C₄₅H₅₆O₁₁
• 分子量: 772.933
• InChiKey: XMXDLGJRHRSHFU-ZYEKJNOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  56.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R)-2-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以81%的产率得到(S)-4-[(2S,3S,4R,5S,6R)-3,4,5-Tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-butane-1,2-diol
  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)-1,2-dideoxy-D-lyxo-hex-1-enitol 在 lead(II) chloride RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 四甲基乙二胺 、 四氯化钛 、 四丁基碘化铵 、 potassium hydride 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.5h， 生成 (2S,3S,4R,5S,6R)-2-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-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