(3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• 英文别名: 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose；2,3:5,6-di-O-isopropylidene 2-C-hydroxymethyl-D-mannofuranose；2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannofuranose；(3aS,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• 化学式: C₁₃H₂₂O₇
• 分子量: 290.313
• InChiKey: SGJOYWAHFNJARE-OSMMZBANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol 在 溴 、 barium carbonate 作用下， 以 水 为溶剂， 以86%的产率得到2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone
  参考文献：
  名称：

  酮糖上的Kiliani：d-果糖和l-山梨糖的支链碳水化合物构件

  摘要：

  经保护的支链糖内酯可通过Kiliani-丙酮化序列在容易获得的酮糖如d-果糖和l-山梨糖上获得。在两种情况下，容易结晶的二丙酮化物在产物内酯中具有2，3-顺-二醇关系。来自d-果糖的产物在C-4和C-5处的构型的有效两次转化使得能够获得来自l--糖的形式Kiliani产物。支链碳水化合物内酯作为具有功能化四元中心的同手性目标的卡隆，可能具有重要的价值。

  DOI：

  10.1016/j.tetlet.2004.10.086
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 甲酸 、 potassium carbonate 作用下， 以 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
  参考文献：
  名称：

  US2014/274930

  摘要：

  公开号：

文献信息

• Kiliani on ketoses: branched carbohydrate building blocks from d-fructose and l-sorbose
  作者：David Hotchkiss、Raquel Soengas、Michela Iezzi Simone、Jeroen van Ameijde、Stuart Hunter、Andrew R. Cowley、George W.J. Fleet

  DOI：10.1016/j.tetlet.2004.10.086

  日期：2004.12

  both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres

  经保护的支链糖内酯可通过Kiliani-丙酮化序列在容易获得的酮糖如d-果糖和l-山梨糖上获得。在两种情况下，容易结晶的二丙酮化物在产物内酯中具有2，3-顺-二醇关系。来自d-果糖的产物在C-4和C-5处的构型的有效两次转化使得能够获得来自l--糖的形式Kiliani产物。支链碳水化合物内酯作为具有功能化四元中心的同手性目标的卡隆，可能具有重要的价值。
• Synthesis of Branched Iminosugars through a Hypervalent Iodine(III)-Mediated Radical-Polar Crossover Reaction
  作者：Andrés G. Santana、Nieves R. Paz、Cosme G. Francisco、Ernesto Suárez、Concepción C. González

  DOI：10.1021/jo401041s

  日期：2013.8.2

  The synthesis of a novel type of branched iminosugars is described. This synthetic strategy is based on two key reactions: first, an aldol reaction with formaldehyde in order to introduce selectively the hydroxymethyl branch, and second, a tandem β-fragmentation-intramolecular cyclization reaction. The combination of both reactions afforded a battery of compounds exhibiting a great structural complexity

  描述了新型的支链亚氨基糖的合成。该合成策略基于两个关键反应：首先是与甲醛的醛醇缩合反应，以选择性地引入羟甲基支链；其次，是串联β-片段化-分子内环化反应。两种反应的结合提供了一系列具有极大结构复杂性的化合物，并伴随着从容易获得的醛糖开始的季中心的形成。通过这种方法，我们已经证明了由PhIO / I 2系统促进的异头烷氧基自由基（ARF）断裂对制备新化合物的用途，这对于医学和合成化学家均具有潜在的意义。
• Synthesis of 2-C-branched derivatives of d-mannose: 2-C-aminomethyl-d-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of d-mannose
  作者：Daniel A. Mitchell、Nigel A. Jones、Stuart J. Hunter、Joseph M.D. Cook、Sarah F. Jenkinson、Mark R. Wormald、Raymond A. Dwek、George W.J. Fleet

  DOI：10.1016/j.tetasy.2007.06.003

  日期：2007.7

  2-C-Substituted branched D-mannose analogues are novel monosaccharides, readily obtained from a Kiliani-acetonation sequence on D-fructose, followed by subsequent functional group manipulation. 2-C-Azidomethyl-D-mannose and 2-C-aminomethylD-marmose bind to the C-type lectin DC-SIGN (CD209) with significantly greater affinity than mannose. In particular, 2-C-aminomethyl-D-mannose exhibits a comparative 48-fold increase in binding as determined using a surface plasmon resonance-based competition assay. DC-SIGN is an important cell-surface type II transmembrane protein that interacts with blood group antigens, endogenous glycoproteins such as ICAM-3, and also deadly pathogens such as the human immunodeficiency and hepatitis C viruses. The effective use of small compounds to block target binding by mannose-selective C-type lectins at sub-millimolar concentrations has not been shown previously; thus, these data represent a very attractive thoroughfare to novel antiviral and immunomodulatory drug development. @ 2007 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of (−)- and (+)-pentenomycins using RCM
  作者：G. Venkata Ramana、B. Venkateswara Rao

  DOI：10.1016/s0040-4039(03)01132-8

  日期：2003.6

  An efficient synthesis of enantiopure (-)- and (+)-pentenomycins are described by reductive iodo elimination and ring-closing metathesis (RCM), as the key steps. The first synthesis of the unnatural (+)-isomer is described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• ——
  作者：E. E. Nifant'ev、E. V. Lipovtsin、T. V. Dudakova、A. S. Shashkov、M. P. Koroteev

  DOI：10.1023/a:1021731911711

  日期：——