(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

• 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。
• <i>C</i>-Branched Iminosugars: α-Glucosidase Inhibition by Enantiomers of isoDMDP, isoDGDP, and isoDAB–<scp>l</scp>-isoDMDP Compared to Miglitol and Miglustat
  作者：Sarah F. Jenkinson、Daniel Best、A. Waldo Saville、James Mui、R. Fernando Martínez、Shinpei Nakagawa、Takahito Kunimatsu、Dominic S. Alonzi、Terry D. Butters、Caroline Norez、Frederic Becq、Yves Blériot、Francis X. Wilson、Alexander C. Weymouth-Wilson、Atsushi Kato、George W. J. Fleet

  DOI：10.1021/jo4005487

  日期：2013.8.2

  The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 4596 from D-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K-i 0.081 mu M for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.
• 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：——