(2R,3S)-6-(benzyloxy)-1,2-dihydroxyhexan-3-yl benzoate | 902128-50-1

• 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: (2R,3S)-6-(benzyloxy)-1,2-dihydroxyhexan-3-yl benzoate
• 英文别名: [(2R,3S)-1,2-dihydroxy-6-phenylmethoxyhexan-3-yl] benzoate
• CAS: 902128-50-1
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: XZWKPZJKGYQPBP-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-6-(benzyloxy)-1,2-dihydroxyhexan-3-yl benzoate 在 4-二甲氨基吡啶 、 乙基溴化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,2-Dimethyl-propionic acid (2R,3S)-6-benzyloxy-2,3-dihydroxy-hexyl ester
  参考文献：
  名称：

  Enantioselective total synthesis of aigialomycin D

  摘要：

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.027
• 作为产物：
  描述：

  6-(苄氧基)己-2-炔-1-醇 在 titanium(IV) isopropylate 、 (-)-diisopropyl tartrate titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 calcium hydride 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 (2R,3S)-6-(benzyloxy)-1,2-dihydroxyhexan-3-yl benzoate
  参考文献：
  名称：

  Enantioselective total synthesis of aigialomycin D

  摘要：

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.027

文献信息

• Enantioselective total synthesis of aigialomycin D
  作者：Jiangping Lu、Junying Ma、Xingang Xie、Bo Chen、Xuegong She、Xinfu Pan

  DOI：10.1016/j.tetasy.2006.03.027

  日期：2006.4

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.