(R)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)prop-2-en-1-ol | 22144-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)prop-2-en-1-ol
• 英文别名: 1,2:3,4-Bis-O-isopropyliden-6-hepten-D-manno-1,2,3,4,5-pentol；(1R)-1-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 22144-64-5
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: SWUCOESSUIAFQV-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)prop-2-en-1-ol 在 碳酸氢钠 、 sodium sulfate 、 高碘酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 tert-butyl benzyl((R)-1-((4R,5R)-5-((R)-1-hydroxyallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate
  参考文献：
  名称：

  Stereoselective synthesis of N-benzyl conduramine F-1, N-benzyl ent-conduramine E-1, dihydroconduramine F-1 and ent-dihydroconduramine E-1

  摘要：

  A short and stereoselective synthesis of conduramine F-1 and ent-conduramine E-1 derivatives have been achieved starting from D-mannitol using nucleophilic vinylation on imine. A concise sequence of vinylation at both ends of D-mannitol and followed by RCM allowed us to prepare target compound. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.12.082
• 作为产物：
  描述：

  (S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethane-1,2-diol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.25h， 生成 (R)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of N-benzyl conduramine F-1, N-benzyl ent-conduramine E-1, dihydroconduramine F-1 and ent-dihydroconduramine E-1

  摘要：

  A short and stereoselective synthesis of conduramine F-1 and ent-conduramine E-1 derivatives have been achieved starting from D-mannitol using nucleophilic vinylation on imine. A concise sequence of vinylation at both ends of D-mannitol and followed by RCM allowed us to prepare target compound. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.12.082

文献信息

• Asymmetric Syntheses of Chiral Allylic Alcohols
  作者：Christiane Schneider、Uli Kazmaier

  DOI：10.1055/s-1998-6103

  日期：1998.9
• Stereoselective synthesis of N-benzyl conduramine F-1, N-benzyl ent-conduramine E-1, dihydroconduramine F-1 and ent-dihydroconduramine E-1
  作者：Ramakrishna Katakam、Rajender Anugula、Lingamurthy Macha、Venkateswara Rao Batchu

  DOI：10.1016/j.tetlet.2016.12.082

  日期：2017.2

  A short and stereoselective synthesis of conduramine F-1 and ent-conduramine E-1 derivatives have been achieved starting from D-mannitol using nucleophilic vinylation on imine. A concise sequence of vinylation at both ends of D-mannitol and followed by RCM allowed us to prepare target compound. (C) 2017 Elsevier Ltd. All rights reserved.