(2S,3R,4R,5R)-5-methyl-2,3,4-tris(phenylmethoxy)cyclohexan-1-one | 144668-26-8

• 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: (2S,3R,4R,5R)-5-methyl-2,3,4-tris(phenylmethoxy)cyclohexan-1-one
• CAS: 144668-26-8
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: ABGCPWIKKYVFDB-WWAFRDAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-5-methyl-2,3,4-tris(phenylmethoxy)cyclohexan-1-one 在 四氮唑 、 sodium tetrahydroborate 、 cerium(III) chloride 、 氨 、 lithium 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 [[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(1S,2S,3R,4R,5R)-2,3,4-trihydroxy-5-methylcyclohexyl] hydrogen phosphate
  参考文献：
  名称：

  Synthesis of carbocyclic analogs of guanosine 5'-(.beta.-L-fucopyranosyl diphosphate) (GDP-fucose) as potential inhibitors of fucosyltransferases.

  摘要：

  Two carbocyclic analogues of GDP-fucose consisting of 5a-carba-beta-L-fucopyranose and its unsaturated counterpart have been synthesized as potential inhibitors of fucosyltransferases through the intramolecular Emmons-Horner-Wadsworth olefination of the 2,6-dioxo-phosphonate derivative, readily available from L-fucose, followed by chemo- and stereoselective reductions of the alpha,beta-unsaturated inosose intermediate, which are the critical steps.

  DOI：

  10.1021/jo00051a004
• 作为产物：
  描述：

  (3S,4R,5S)-1-dimethoxyphosphoryl-3,4,5-tris(phenylmethoxy)heptane-2,6-dione 在 hydrido(triphenylphosphine)copper(I) hexamer 、 sodium hydride 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 、 水 为溶剂， 反应 49.0h， 生成 (2S,3R,4R,5R)-5-methyl-2,3,4-tris(phenylmethoxy)cyclohexan-1-one
  参考文献：
  名称：

  Synthesis of carbocyclic analogs of guanosine 5'-(.beta.-L-fucopyranosyl diphosphate) (GDP-fucose) as potential inhibitors of fucosyltransferases.

  摘要：

  Two carbocyclic analogues of GDP-fucose consisting of 5a-carba-beta-L-fucopyranose and its unsaturated counterpart have been synthesized as potential inhibitors of fucosyltransferases through the intramolecular Emmons-Horner-Wadsworth olefination of the 2,6-dioxo-phosphonate derivative, readily available from L-fucose, followed by chemo- and stereoselective reductions of the alpha,beta-unsaturated inosose intermediate, which are the critical steps.

  DOI：

  10.1021/jo00051a004

文献信息

• The stereoselective syntheses of 1-aryl-1,6-dideoxyinositol derivatives
  作者：Jianwei Bian、Steven R. Schneider、Robert J. Maguire

  DOI：10.1016/j.tetlet.2011.07.066

  日期：2011.10

  This Letter describes the first report of a highly stereoselective synthesis of triethereal cyclohexanones via copper(I) mediated 1,4-addition of organometallic reagents to glucose-derived triethereal cyclohexenone. The cyclohexanones generated can be reduced with modest stereoselectivity to afford a variety of substituted inositol derivatives as potential pyranose sugar mimetics. The protocol generated

  这封信描述了通过铜（I）介导的有机金属试剂向葡萄糖衍生的三醚环己烯酮的1,4-加成反应高度立体选择性地合成三醚环己酮的第一个报道。可以以适度的立体选择性还原所产生的环己酮，以提供各种取代的肌醇衍生物作为潜在的吡喃糖模拟物。该方案以单一立体异构体的高收率生成了一系列取代的环己酮。