(2S,4R,6S)-6-methyl-2-(tosyloxymethyl)tetrahydro-2H-pyran-4-ol | 1092105-42-4

• 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: (2S,4R,6S)-6-methyl-2-(tosyloxymethyl)tetrahydro-2H-pyran-4-ol
• 英文别名: (2S,4R,6S)-(4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate；[(2S,4R,6S)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]methyl 4-toluenesulfonate；[(2S,4R,6S)-4-hydroxy-6-methyloxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1092105-42-4
• 化学式: C₁₄H₂₀O₅S
• 分子量: 300.376
• InChiKey: VRHFWSGDAGSESX-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R,6S)-6-methyl-2-(tosyloxymethyl)tetrahydro-2H-pyran-4-ol 、 氯甲基甲基醚 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到[(2S,4R,6S)-4-(methoxymethoxy)-6-methyltetrahydro-2H-pyran-2-yl]methyl 4-toluenesulfonate
  参考文献：
  名称：

  Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation

  摘要：

  A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.

  DOI：

  10.1055/s-0029-1218679
• 作为产物：
  描述：

  (2S,4R,6S)-2-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-4-ol 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(2S,4R,6S)-6-methyl-2-(tosyloxymethyl)tetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  通过Prins环化立体选择性合成（10S，12S）-10-羟基-12-甲基-1-氧杂环十二烷-2,5-二酮

  摘要：

  描述了（10 S，12 S）-10-羟基-12-甲基-1-氧杂环十二烷-2,5-二酮的全合成，证明了Prins环化在天然产物合成中的多功能性。该方法是收敛的且高度立体选择性的。王子的环化，酯化，闭环复分解和氧化反应被用作合成该大内酯的关键步骤。 王子环化-酯化-闭环复分解-大内酯

  DOI：

  10.1055/s-0029-1217107

文献信息

• The stereoselective total synthesis of xestodecalactone C and epi-sporostatin via the Prins cyclisation
  作者：J.S. Yadav、N. Thrimurtulu、K. Uma Gayathri、B.V. Subba Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2008.08.096

  日期：2008.11

  Syntheses of xestodecalactone C and epi-sporostatin are described utilising Prins cyclisations, Mitsunobu reaction and intramolecular Friedel–Crafts acylation. The approach is convergent and highly stereoselective.

  使用Prins环化，Mitsunobu反应和分子内Friedel-Crafts酰化作用描述了异黄酮内酯C和Epi- sporostatin的合成。该方法是收敛的和高度立体选择性的。
• Total synthesis of (+)-pseudohygroline
  作者：J.S. Yadav、G. Narasimhulu、N. Mallikarjuna Reddy、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2010.01.060

  日期：2010.3

  A simple and efficient total synthesis of five-membered pyrrolidine, (+)-pseudohygroline is described. The key steps involved in this synthesis are highly stereoselective Prins cyclisation followed by reductive ring opening and hydroboration. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of (10S,12S)-10-Hydroxy-12-methyl-1-oxacyclo­dodecane-2,5-dione via Prins Cyclization
  作者：J. Yadav、N. Thrimurtulu、M. Venkatesh、K. Rao、A. Prasad、B. Reddy

  DOI：10.1055/s-0029-1217107

  日期：2010.1

  The total synthesis of (10S,12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione is described proving the versatility of the Prins cyclization in natural products synthesis. The approach is convergent and highly stereoselective. Prins cyclization, esterification, ring-closing metathesis and oxidation reactions are utilized as key steps in the synthesis of this macrolactone. Prins cyclization - esterification

  描述了（10 S，12 S）-10-羟基-12-甲基-1-氧杂环十二烷-2,5-二酮的全合成，证明了Prins环化在天然产物合成中的多功能性。该方法是收敛的且高度立体选择性的。王子的环化，酯化，闭环复分解和氧化反应被用作合成该大内酯的关键步骤。 王子环化-酯化-闭环复分解-大内酯
• Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation
  作者：Jhillu Yadav、N. Reddy、P. Reddy、Hissana Ather、Attaluri Prasad

  DOI：10.1055/s-0029-1218679

  日期：2010.5

  A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.