6-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethoxymethyl]-2,3-dihydro-1,4-dithiine-5-carbaldehyde | 915374-59-3

• 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: 6-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethoxymethyl]-2,3-dihydro-1,4-dithiine-5-carbaldehyde
• CAS: 915374-59-3
• 化学式: C₁₈H₂₂O₄S₂
• 分子量: 366.502
• InChiKey: XABLIHGFCOEIGI-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethoxymethyl]-2,3-dihydro-1,4-dithiine-5-carbaldehyde 在 Oxone 、 高氯酸 、 Amberlyst 15 、 edetate disodium 、 镍 、 碳酸氢钠 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 21.5h， 生成 methyl 4-O-benzyl-α-L-altropyranoside
  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：

  (S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](3-[(4-methoxybenzyl)oxy]methyl-5,6-dihydro-1,4-dithiin-2-yl)methanol 在 Celite 、 sodium hydride 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 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

文献信息

• Rapid Access to 1,6-Anhydro-β-<scp>l</scp>-hexopyranose Derivatives via Domino Reaction: Synthesis of <scp>l</scp>-Allose and <scp>l</scp>-Glucose
  作者：Daniele D’Alonzo、Annalisa Guaragna、Carmela Napolitano、Giovanni Palumbo

  DOI：10.1021/jo800775v

  日期：2008.7.1

  An expeditious and efficient synthesis of 1,6-anhydro-beta-L-hexopyranosyl derivatives 3 as valuable building blocks for the preparation Of L-sugars is herein reported. This route relies upon the use of a domino reaction involving five synthetic steps from the 5,6-dihydro-1,4-dithiin 4. As 1,6-anhydro derivatives 3 are obtained, dithioethylene bridge removal and double-bond dihydroxylation give access to protected L-allose and L-glucose in stereoselective fashion and high yields.