(1R,4R,5R,6R)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol | 144732-65-0

• 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: (1R,4R,5R,6R)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol
• CAS: 144732-65-0
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: GVURPUYMWIRVRI-BIYDSLDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4R,5R,6R)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到Carba-α-L-fucopyranose
  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：

  (3R,4R,5R,6S)-1-dimethoxyphosphoryl-3,4,5-tris(phenylmethoxy)heptane-2,6-diol 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 5.5h， 生成 (1R,4R,5R,6R)-3-methyl-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol
  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