(-)-1,2,6-Hexanetriol | 130232-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-1,2,6-Hexanetriol
• 英文别名: (2S)-hexane-1,2,6-triol
• CAS: 130232-56-3
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: ZWVMLYRJXORSEP-LURJTMIESA-N

物化性质

• 沸点：
  323.1±0.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-1,2,6-Hexanetriol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 camphor-10-sulfonic acid 、 双氧水 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  First stereoselective total synthesis of triumfettamide

  摘要：

  The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units-alpha-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.068
• 作为产物：
  描述：

  5-己烯-1-醇 在 potassium osmate(VI) dihydrate 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以96%的产率得到(-)-1,2,6-Hexanetriol
  参考文献：
  名称：

  First stereoselective total synthesis of triumfettamide

  摘要：

  The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units-alpha-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.068

文献信息

• Synthesis of some trideoxy- d -hexoses and derivatives thereof from d -glucono-1,5-lactone
  作者：Henk Regeling、Gordon J. F. Chittenden

  DOI：10.1016/0008-6215(92)84152-i

  日期：1992.9

  methyl 2,3,4-trideoxy-α- d - and -β- d -glycero-hexopyranoside (10 and 11) methyl α- d - and β- d -amicetopyranoside (24 and 25), (2S)-1,2-hexanediol (36), (2S)-1,2,6-hexanetriol (37), and some derivatives thereof from d -glucono-1,5-lactone are described.

  摘要甲基2,3,4-丁氧基-α-d-和-β-d-甘油己吡喃糖苷（10和11）甲基α-d-和β-d-乙酰吡喃糖苷（24和25），（2S描述了）-1,2-己二醇（36），（2S）-1,1,2,6-己三醇（37），以及它们的一些衍生自d-葡萄糖基-1,5-内酯的衍生物。
• Dispiroketals in synthesis (part 9): Resolution of 1,2-diols using a C2-symmetric diphenyltetrahydrobipyran.
  作者：Paul J. Edwards、David A. Entwistle、Steven V. Ley、Dafydd R. Owen、Emily J. Perry

  DOI：10.1016/0957-4166(94)80016-2

  日期：1994.4

  A series of 1,2-diols were resolved by the enantioselective formation of the thermodynamically most stable dispiroketal using (2R,2'R) and (2S,2'S) 2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'- 2 and 3. Deprotection was achieved using a metal ammonia reduction to liberate the resolved diols.
• On the stereochemistry of palmerolide A
  作者：Matthew D. Lebar、Bill J. Baker

  DOI：10.1016/j.tetlet.2007.09.053

  日期：2007.11

  Degradative studies of the anticancer macrolide palmerolide A have resulted in re-assignment of the C-7,C-10, and C-11 stereocenters. (c) 2007 Elsevier Ltd. All rights reserved.
• A General, Practical, and Versatile Strategy for Accessing ω-Functional 1,2-Diols of High Enantiomeric Excess
  作者：Thomas R. Hoye、Michael J. Mayer、Tricia J. Vos、Zhixiong Ye

  DOI：10.1021/jo980844p

  日期：1998.11.1
• First stereoselective total synthesis of triumfettamide
  作者：Thongam Joymati Devi、Bishwajit Saikia、Nabin C. Barua

  DOI：10.1016/j.tet.2013.08.068

  日期：2013.11

  The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units-alpha-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1. (C) 2013 Elsevier Ltd. All rights reserved.