(R)-4-(3-[1,3]Dithian-2-yl-propyl)-2,2-dimethyl-[1,3]dioxolane | 900519-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-(3-[1,3]Dithian-2-yl-propyl)-2,2-dimethyl-[1,3]dioxolane
• 英文别名: (4R)-4-[3-(1,3-dithian-2-yl)propyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 900519-20-2
• 化学式: C₁₂H₂₂O₂S₂
• 分子量: 262.437
• InChiKey: AWCVZBPVGYNBID-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-(3-[1,3]Dithian-2-yl-propyl)-2,2-dimethyl-[1,3]dioxolane 在 sodium tetrahydroborate 、 strontium(II) carbonate 、 叔丁基锂 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 、 正戊烷 为溶剂， 反应 1.5h， 生成 (E)-(S)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methyl-tridec-7-en-4-ol
  参考文献：
  名称：

  Unified Total Synthesis of Pteriatoxins and Their Diastereomers

  摘要：

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

  DOI：

  10.1021/ja0618954
• 作为产物：
  描述：

  (R)-2,2-二甲基-1,3-二氧戊环-4-丙醇 在 咪唑 、 六甲基磷酰三胺 、 碘 、 叔丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 4.0h， 生成 (R)-4-(3-[1,3]Dithian-2-yl-propyl)-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  Unified Total Synthesis of Pteriatoxins and Their Diastereomers

  摘要：

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

  DOI：

  10.1021/ja0618954

文献信息

• Enantiomeric Synthesis of the SPIKET-P Enantiomers
  作者：Subrata Chattopadhyay、Anubha Sharma、Prema Iyer、Sunita Gamre

  DOI：10.1055/s-2004-822342

  日期：——

  A convenient synthesis of the antipodes of the title compound has been developed starting from (R)-1,2,5,6-dicyclohexylidene mannitol. Some of the key features of the syntheses were simple reaction protocols, and stereoselective inversion of chiral 1,2-diol moiety via neighbouring group assisted acetylation.

  从 (R)-1,2,5,6-二亚环己基甘露醇开始，开发了标题化合物对映体的简便合成方法。合成的一些关键特征是简单的反应方案，以及通过相邻基团辅助乙酰化的手性 1,2-二醇部分的立体选择性反转。
• Unified Total Synthesis of Pteriatoxins and Their Diastereomers
  作者：Fumiyoshi Matsuura、René Peters、Masahiro Anada、Scott S. Harried、Junliang Hao、Yoshito Kishi

  DOI：10.1021/ja0618954

  日期：2006.6.1

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.