(4S,6R)-4-benzyl-6-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxane | 219746-26-6

• 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: (4S,6R)-4-benzyl-6-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxane
• 英文别名: (4S,6R)-4-benzyl-2,2-dimethyl-6-(phenylmethoxymethyl)-1,3-dioxane
• CAS: 219746-26-6
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: ZYNHKUNSVHIICK-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,6R)-4-benzyl-6-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxane 在 4-二甲氨基吡啶 、 氨 、 碳酸氢钠 、 calcium 、 三乙胺 、 lithium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4S,6R)-4-benzyl-6-(iodomethyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Iterative asymmetric synthesis of protected anti-1,3-polyols

  摘要：

  A new general method for the iterative asymmetric synthesis of anti-1,3-polyol chains has been developed. The alpha,alpha'-bisalkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP-hydrazone 1 with benzyloxymethylchloride as the second electrophile leads to virtually diastereo- and enantiopure substituted 2,2-dimethyl-1,3-dioxan-5-ones with good overall yields. Their deoxygenation and conversion into primary iodides affords the electrophile for the further alkylation of 1. In this way the configurations of all new stereogenic centres are controlled by a single auxiliary. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00645-0
• 作为产物：
  描述：

  在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以91%的产率得到(4S,6R)-4-benzyl-6-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Iterative asymmetric synthesis of protected anti-1,3-polyols

  摘要：

  A new general method for the iterative asymmetric synthesis of anti-1,3-polyol chains has been developed. The alpha,alpha'-bisalkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP-hydrazone 1 with benzyloxymethylchloride as the second electrophile leads to virtually diastereo- and enantiopure substituted 2,2-dimethyl-1,3-dioxan-5-ones with good overall yields. Their deoxygenation and conversion into primary iodides affords the electrophile for the further alkylation of 1. In this way the configurations of all new stereogenic centres are controlled by a single auxiliary. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00645-0

文献信息

• Synthesis of (3<i>R</i>,5<i>R</i>)-harzialactone A and its (3<i>R</i>,5<i>S</i>)-isomer
  作者：Gowravaram Sabitha、Rangavajjula Srinivas、Sukant K Das、Jhillu S Yadav

  DOI：10.3762/bjoc.6.8

  日期：——

  The total synthesis of (3R,5R)-harzialactone A (1) and its (3R,5S)-isomer (2) is described. Epoxide opening with thioacetal and diastereoselective reductions are used as key reactions.

  报道了(3R,5R)-harzialactone A (1)及其(3R,5S)-异构体(2)的全合成。关键反应包括硫代醇和立体选择性还原的环氧开放反应。