{3-[(S)-Benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-[1,4]dithiin-2-yl}-methanol | 915374-58-2

• 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: {3-[(S)-Benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-[1,4]dithiin-2-yl}-methanol
• 英文别名: [6-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethoxymethyl]-2,3-dihydro-1,4-dithiin-5-yl]methanol
• CAS: 915374-58-2
• 化学式: C₁₈H₂₄O₄S₂
• 分子量: 368.518
• InChiKey: VJHJUNILAAQYIQ-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {3-[(S)-Benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-[1,4]dithiin-2-yl}-methanol 在 Celite 、 pyridinium chlorochromate 作用下， 以 吡啶 为溶剂， 反应 8.0h， 以99%的产率得到6-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethoxymethyl]-2,3-dihydro-1,4-dithiine-5-carbaldehyde
  参考文献：
  名称：

  A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

  摘要：

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

  DOI：

  10.1021/ol061916z
• 作为产物：
  描述：

  5,6-dihydro-1,4-dithiin-2-yl-[(4-methoxybenzyl)oxy]methane 在 正丁基锂 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 {3-[(S)-Benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-[1,4]dithiin-2-yl}-methanol
  参考文献：
  名称：

  A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

  摘要：

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

  DOI：

  10.1021/ol061916z

文献信息

• A Versatile Route to <scp>l</scp>-Hexoses:  Synthesis of <scp>l</scp>-Mannose and <scp>l</scp>-Altrose
  作者：Annalisa Guaragna、Carmela Napolitano、Daniele D'Alonzo、Silvana Pedatella、Giovanni Palumbo

  DOI：10.1021/ol061916z

  日期：2006.10.1

  [GRAPHICS]An efficient route for the synthesis of orthogonally protected L-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-L-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-L-pyranoside, which can be suitably functionalized to afford the desired L-hexoses. In this paper, we report the synthesis of L-manno- and L-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.