2,3:5,6-di-O-isopropylidene-2-C-methyl-D-mannono-1,4-lactone | 949573-77-7

• 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-methyl-D-mannono-1,4-lactone
• 英文别名: (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,3a-trimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one；(3aS,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,3a-trimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• CAS: 949573-77-7
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: GRWXMIGCVRUFNZ-SKNMHBRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  1
• 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-methyl-D-mannono-1,4-lactone 以 二氯甲烷 、 甲苯 为溶剂， 以98%的产率得到2,3:5,6-di-O-isopropylidene-2-C-methyl-D-mannofuranose
  参考文献：
  名称：

  US2014/274930

  摘要：

  公开号：
• 作为产物：
  描述：

  2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone 在 sodium thiosulfate 、 三苯基膦 作用下， 以 乙醇 、 正己烷 、 正庚烷 、 二氯甲烷 、 甲苯 为溶剂， 生成 2,3:5,6-di-O-isopropylidene-2-C-methyl-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.
• 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
• US9890176B2
  申请人：——

  公开号：US9890176B2

  公开（公告）日：2018-02-13