(4S,6S)-4-(tert-Butyldimethylsiloxy)-6-hydroxy-1-heptene | 136444-77-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4S,6S)-4-(tert-Butyldimethylsiloxy)-6-hydroxy-1-heptene
• 英文别名: (2S,4S)-4-((tert-butyldimethylsilyl)oxy)hept-6-en-2-ol；(2S,4S)-4-(tert-butyldimethylsilanyloxy)hept-6-en-2-ol；(2S,4S)-4-[tert-butyl(dimethyl)silyl]oxyhept-6-en-2-ol
• CAS: 136444-77-4
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: NQBRYEKHYFTIQR-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,6S)-4-(tert-Butyldimethylsiloxy)-6-hydroxy-1-heptene 在 2,6-二甲基吡啶 、 gold(III) chloride 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 2-((2R,4R,6S)-4-((tert-butyldimethylsilyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)acetaldehyde
  参考文献：
  名称：

  通过顺序烯丙基化策略全合成四酮和隐三叶酚I

  摘要：

  已经从商业上可得的起始原料成功地为11步和17步设计了统一的高效合成四酮化合物（1）和隐秘三氟酚I（2）的合成路线，总收率分别为16％和11％。合成的亮点涉及连续的路易斯酸催化的高度区域和非对映选择性的烯丙基化和分子内光延内酯化。

  DOI：

  10.1021/acs.jnatprod.6b00443
• 作为产物：
  描述：

  (4S,6S)-4-Hydroxy-6-(benzyloxy)-1-heptene 在 咪唑 、 氨 、 sodium 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (4S,6S)-4-(tert-Butyldimethylsiloxy)-6-hydroxy-1-heptene
  参考文献：
  名称：

  Total synthesis of (-)-colletol

  摘要：

  The first total synthesis of the unsymmetrical bis-macrolide (-)-colletol is described. The synthesis involves a Lewis acid mediated addition of triphenylallylstannane to aldehyde 14 to set the C12 stereochemistry. The penultimate step utilized macrolactonization to assemble the 14-membered ring. The natural product was prepared in 12 linear steps and 12% overall yield.

  DOI：

  10.1021/jo00023a029

文献信息

• 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
• 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.
• Total synthesis of (-)-colletol
  作者：Gary E. Keck、Jerry A. Murry

  DOI：10.1021/jo00023a029

  日期：1991.11

  The first total synthesis of the unsymmetrical bis-macrolide (-)-colletol is described. The synthesis involves a Lewis acid mediated addition of triphenylallylstannane to aldehyde 14 to set the C12 stereochemistry. The penultimate step utilized macrolactonization to assemble the 14-membered ring. The natural product was prepared in 12 linear steps and 12% overall yield.
• Total Synthesis of Tetraketide and Cryptorigidifoliol I via a Sequential Allylation Strategy
  作者：Birakishore Padhi、G. Sudhakar Reddy、Debendra K. Mohapatra

  DOI：10.1021/acs.jnatprod.6b00443

  日期：2016.11.23

  cryptorigidifoliol I (2) has been devised successfully from commercially available starting materials in 11 and 17 steps, with 16% and 11% overall yields, respectively. Highlights of the syntheses involved sequential Lewis acid-catalyzed highly regio- and diastereoselective allylations and intramolecular Mitsunobu lactonization.

  已经从商业上可得的起始原料成功地为11步和17步设计了统一的高效合成四酮化合物（1）和隐秘三氟酚I（2）的合成路线，总收率分别为16％和11％。合成的亮点涉及连续的路易斯酸催化的高度区域和非对映选择性的烯丙基化和分子内光延内酯化。