2,3:5,6-di-O-isopropylidene-2-C-iodomethyl-D-mannono-1,4-lactone | 949573-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:5,6-di-O-isopropylidene-2-C-iodomethyl-D-mannono-1,4-lactone
• 英文别名: (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(iodomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one；(3aS,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3a-(iodomethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• CAS: 949573-76-6
• 化学式: C₁₃H₁₉IO₆
• 分子量: 398.195
• InChiKey: LBMFZQYLFOIZLT-SKNMHBRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3:5,6-di-O-isopropylidene-2-C-iodomethyl-D-mannono-1,4-lactone 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 、 二异丙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -72.0~80.0 ℃ 、101.33 kPa 条件下， 反应 56.0h， 生成
  参考文献：
  名称：

  (-)-Furospongin-1 和 (+)-Dihydrofurospongin-2 的合成和构型

  摘要：

  首次使用基于手性池的路线合成了众所周知的呋喃萜类 furospongin-1 和 dihydrofurospongin-2，以确保先前的构型分配。关键的C-11立体中心取自D-甘露糖，利用甘露糖的手性安装C-13烷基中心。由于所用构件的去质子化和/或烯醇化，呋喃部分的引入是有问题的，因此必须避免一些反应。使用 Julia-Kocienski 烯化在 1,2-二甲氧基乙烷中最令人满意地构建了三取代烯烃，使用仲砜实现了最佳 (E)/(Z) 比。合成样品不仅为这两种天然产物的 C-13 构型提供了第一个明确的证据，

  DOI：

  10.1002/ejoc.201501489
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 甲酸 、 溴 、 potassium carbonate 、 caesium carbonate 、 sodium thiosulfate 、 三苯基膦 作用下， 以 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 生成 2,3:5,6-di-O-isopropylidene-2-C-iodomethyl-D-mannono-1,4-lactone
  参考文献：
  名称：

  US2014/274930

  摘要：

  公开号：

文献信息

• Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
  作者：K. Victoria Booth、Sarah F. Jenkinson、Daniel Best、Fernando Fernández Nieto、Ramón J. Estévez、Mark R. Wormald、Alexander C. Weymouth-Wilson、George W.J. Fleet

  DOI：10.1016/j.tetlet.2009.06.098

  日期：2009.9

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme
  作者：Nigel A. Jones、Devendar Rao、Akihide Yoshihara、Pushpakiran Gullapalli、Kenji Morimoto、Goro Takata、Stuart J. Hunter、Mark R. Wormald、Raymond A. Dwek、Ken Izumori、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.07.034

  日期：2008.8

  The Kiliani synthesis oil the 4 readily accessible ketohexoses (D-fructose, D-tagatose, L-sorbose, D-psicose) allows access to 4 diastereomeric 2-C-methyl-aldohexoses (2-C-methyl-D-mannose, 2-C-methyl-D-talose, 2-C-methyl-L-gulose, 2-C-methyl-D-allose) and 4 diastereomeric 2-C-methyl-alditols (2-C-methyl-mannitol, 2-C-methyl-D-talitol, 2-C-methyl-L-gulitol, 2-C-methyl-D-allitol). Microbial oxidation of 2-C-methyl-D-mannitol and 2-C-metllyl-L-gulitol gave 5-C-methyl-D-fructose; Microbial oxidation of 2-C-methyl-D-talitol afforded 5-C-methyl-D-psicose, whereas 2-C-methyl-D-allitol formed 5-C-methyl-Lpsicose. Both enantiomers of 5-C-methyl-fructose were equilibrated by D-tagatose-3-epimerase (DTE) with both enantiomers of 5-C-methyl-psicose. These transformations demonstrate that polyol dehydrogenases and DTE act on branched synthetic sugars. Full NMR analyses show that 5-C-methyl-D-fructose is present as the P-pyranose and P-furanose forms in a ratio of 90:10; all pyranose and furanose forms of 5-C-methyl-D-psicose are present in solution. The combination of chemical and biological procedures allows the environmentally friendly generation of a new family of branched monosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.
• US20140274930A1
  申请人：——

  公开号：——

  公开（公告）日：——
• MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP2970353A2

  公开（公告）日：2016-01-20