(S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane | 1053718-67-4

• 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: (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane
• 英文别名: (4S)-2,2-dimethyl-4-[3-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxybut-3-enyl]-1,3-dioxolane
• CAS: 1053718-67-4
• 化学式: C₃₆H₄₄O₆
• 分子量: 572.742
• InChiKey: OPVKEPZLHDLOBL-FLLNZLDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane 在 palladium on activated charcoal RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 氢气 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 60.0 ℃ 、379.21 kPa 条件下， 反应 14.0h， 生成 (2R,3S,4R)-6-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3,4-bis-(4-methoxy-benzyloxy)-2-(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
• 作为产物：
  描述：

  二溴甲烷 、 3-(2,2-dimethyl-[1,3]dioxolan-4-yl)propionic acid 2,3-bis(benzyloxy)-1-(benzyloxymethyl)pent-4-enyl ester 在 lead(II) chloride 四甲基乙二胺 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-4-[3-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolane
  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.