(3S)-3-tert-butyldiphenylsilyloxy-pent-5-enoic acid | 929554-04-1

• 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: (3S)-3-tert-butyldiphenylsilyloxy-pent-5-enoic acid
• 英文别名: (3S)-3-(tert-butyldiphenylsilyloxy)pent-4-enoic acid；(3S)-3-[(tert-Butyldiphenylsilyl)oxy]pent-4-enoic acid；(3S)-3-[tert-butyl(diphenyl)silyl]oxypent-4-enoic acid
• CAS: 929554-04-1
• 化学式: C₂₁H₂₆O₃Si
• 分子量: 354.521
• InChiKey: RVRVFVNPRQDCBG-QGZVFWFLSA-N

物化性质

• 沸点：
  436.4±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-tert-butyldiphenylsilyloxy-pent-5-enoic acid 在 吡啶 、 2,4,6-三氯苯甲酰氯 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 (1R)-hept-6-en-2-yl (3S)-3-hydroxy-4-pentenoate
  参考文献：
  名称：

  Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach

  摘要：

  Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.045
• 作为产物：
  描述：

  甲基-2-脱氧-D-核糖 在 indium(III) triflate 、 吡啶 、 咪唑 、 间氯过氧苯甲酸 、 sodium iodide 、 锌 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.5h， 生成 (3S)-3-tert-butyldiphenylsilyloxy-pent-5-enoic acid
  参考文献：
  名称：

  2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks

  摘要：

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.

  DOI：

  10.1021/jo0712143

文献信息

• Enantiospecific synthesis of functionalized polyols from tartaric acid using Ley's dithiaketalization: Application to the total synthesis of achaetolide
  作者：Amit K. Bali、Sunil Kumar Sunnam、Kavirayani R. Prasad

  DOI：10.1016/j.tet.2016.11.035

  日期：2016.12

  Synthesis of chiral tetrols and 1,2,4-triols with varied substitutions was accomplished from tartaric acid. Pivotal reaction in the synthesis was the use of Ley's dithianylation of an alkynyl ketone derived from tartaric acid. Application of the strategy was demonstrated in the total synthesis of decanolactone achaetolide.

  由酒石酸合成具有不同取代基的手性四醇和1,2,4-三醇。合成中的关键反应是使用莱特对酒石酸衍生的炔基酮进行二噻烷基化。该策略在癸内酯癸内酯全合成中得到了证明。
• Stereoselective total synthesis of achaetolide and reconfirmation of its absolute configuration
  作者：P. Srihari、B. Kumaraswamy、P. Shankar、V. Ravishashidhar、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.09.070

  日期：2010.11

  The stereoselective total synthesis of achaetolide 1 has been achieved and its absolute stereochemistry has been reconfirmed to be 35,6R,7S,9R configuration. Keck allylation, Sharpless asymmetric dihydroxylation, and ring closing metathesis are the key steps involved in the target synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach
  作者：G.V.M. Sharma、K. Laxmi Reddy

  DOI：10.1016/j.tetasy.2006.11.045

  日期：2006.12

  Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring. (c) 2006 Elsevier Ltd. All rights reserved.
• 2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks
  作者：Dengjin Wang、William A. Nugent

  DOI：10.1021/jo0712143

  日期：2007.9.1

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.