(2R,4R)-di-O-(3,3-pentylidene)-3-O-[(methylthio)thiocarbonyl]arabitol | 684213-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-di-O-(3,3-pentylidene)-3-O-[(methylthio)thiocarbonyl]arabitol
• 英文别名: O-[bis[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]methyl] methylsulfanylmethanethioate
• CAS: 684213-89-6
• 化学式: C₁₇H₃₀O₅S₂
• 分子量: 378.554
• InChiKey: LXBLZWGGUYPWET-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,4R)-di-O-(3,3-pentylidene)-3-O-[(methylthio)thiocarbonyl]arabitol 在 吡啶 、 三乙基硅烷 、 硫酸 、 过氧化苯甲酰 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 (2S,4S)-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-tri-isopropylbenzenesulphonate)
  参考文献：
  名称：

  Short Synthesis of Enantiopure C₂-Symmetric 1,2:4,5-Diepoxypentane and “Pseudo”-C₂-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol

  摘要：

  On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.

  DOI：

  10.1021/jo034374x
• 作为产物：
  描述：

  (2R,4R)-di-O-(3,3-pentylidene)-3-O-p-toluenesulfonylarabitol 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 (2R,4R)-di-O-(3,3-pentylidene)-3-O-[(methylthio)thiocarbonyl]arabitol
  参考文献：
  名称：

  Short Synthesis of Enantiopure C₂-Symmetric 1,2:4,5-Diepoxypentane and “Pseudo”-C₂-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol

  摘要：

  On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.

  DOI：

  10.1021/jo034374x

文献信息

• The Synthesis of AraBOX, a New 4,4′-Bis(oxazoline), from Novel Pentitol-Derived Bis-β-amino Alcohols
  作者：Patrick O’Leary、David Frain、Fiona Kirby、Patrick McArdle

  DOI：10.1055/s-0029-1216731

  日期：——

  phenyl 4,4'-bis(oxazoline) [AraBOX] is described. The novel ligand is prepared in two efficient steps from a bis-[(O-silyl)β-amino alcohol], via conversion into an intermediate bis(benzamide) followed by a one-pot deprotection-activation-ring closure (DARC) oxazoline formation. To our knowledge, this is the first reported synthesis of an oxazoline ring via this DARC method. The synthesis of two precursor

  描述了新型苯基 ​​4,4'-双(恶唑啉) [AraBOX] 的制备。新型配体由双-[(O-甲硅烷基)β-氨基醇]通过两个有效步骤制备，通过转化为中间体双（苯甲酰胺），然后是一锅脱保护-活化-闭环（DARC）恶唑啉形成。据我们所知，这是首次报道通过这种 DARC 方法合成恶唑啉环。还描述了两种前体双-β-氨基醇的合成，(2R,4R)-和 meso-2,4-diaminopentane-1,5-diol，分别衍生自 D-(+)-arabitol 和木糖醇.