(4S,6S)-4-[[(4R,6S)-6-benzyl-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-6-(phenylmethoxymethyl)-1,3-dioxan-5-one | 235098-86-9

• 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,6S)-4-[[(4R,6S)-6-benzyl-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-6-(phenylmethoxymethyl)-1,3-dioxan-5-one
• CAS: 235098-86-9
• 化学式: C₂₈H₃₆O₆
• 分子量: 468.59
• InChiKey: FEPVQJLCVRFZPG-NDBXHCKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,6S)-4-[[(4R,6S)-6-benzyl-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-6-(phenylmethoxymethyl)-1,3-dioxan-5-one 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 氨 、 三正丁基氢锡 、 sodium hydride 、 calcium 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 [(4R,6S)-6-((4R,6S)-6-Benzyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-methanol
  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 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氨 、 叔丁基锂 、 三正丁基氢锡 、 草酸 、 碳酸氢钠 、 calcium 、 三乙胺 、 lithium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (4S,6S)-4-[[(4R,6S)-6-benzyl-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-6-(phenylmethoxymethyl)-1,3-dioxan-5-one
  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

• Iterative asymmetric synthesis of protected anti-1,3-polyols
  作者：Dieter Enders、Thomas Hundertmark

  DOI：10.1016/s0040-4039(99)00645-0

  日期：1999.5

  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.