bis[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]methanol | 457630-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]methanol
• CAS: 457630-79-4
• 化学式: C₁₅H₂₈O₅
• 分子量: 288.384
• InChiKey: NZYHEFCWJQTWEZ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  bis[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]methanol 在 三氧化硫吡啶 、 二甲基亚砜 作用下， 以84%的产率得到
  参考文献：
  名称：

  Sulfonium ions as inhibitors of the mycobacterial galactofuranosyltransferase GlfT2

  摘要：

  分析：该文段涉及到关于分枝杆菌细胞壁的核心半乳糖基团，由大约30个半乳糖残基组成，通过交替的β-(1→5)和β-(1→6)连接方式连接。 翻译结果：分枝杆菌细胞壁具有一个核心半半乳糖基团，由大约30个半乳糖残基组成，通过交替的β-(1→5)和β-(1→6)连接方式连接。

  DOI：

  10.1039/c4md00067f
• 作为产物：
  描述：

  (2R,4R)-di-O-(3,3-pentylidene)-3-O-p-toluenesulfonylarabitol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到bis[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]methanol
  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.
• Total Synthesis of Proposed Amphidinolide A via a Highly Selective Ring-Closing Metathesis
  作者：Robert E. Maleczka,、Lamont R. Terrell、Feng Geng、Joseph S. Ward

  DOI：10.1021/ol0262284

  日期：2002.8.1

  [GRAPHIC]A highly convergent synthesis of the proposed structure of amphidinolide A is reported. Instructive applications of several organometallic processes are illustrated, including a highly selective ring-closing metathesis reaction.