2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-xylohex-1-enitol | 72002-92-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-xylohex-1-enitol
• 英文别名: 2-acetoxy-D-gulal triacetate；[(2R,3S,4R)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 72002-92-7
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: CSRHQVSHQIAMPP-XBFCOCLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-xylohex-1-enitol 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以80%的产率得到3,4-6-tri-O-acetyl-1,5-anhydro-D-sorbose E-oxime
  参考文献：
  名称：

  A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters

  摘要：

  Zemplen methanolysis or a three-step protocol comprising hydroxylaminolysis, de-O-acetylation and deoximination smoothly and efficiently convert the benzoylated 2-hydroxy-D-glycals Of D-galactose, L-rhamnose and D-Xylose into their configurationally related 1,5-anhydro-ketoses, thereby providing convenient access to the 1,5-anhydro forms of D-tagatose, L-rhamnulose and D-Xylulose. Invariably obtained as amorphous solids, they are best characterized through their highly crystalline oximes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.016

文献信息

• Promotion of a Reaction by Cooling: Stereoselective 1,2‐<i>cis</i>‐α‐Thioglycoconjugation by Thiol‐Ene Coupling at −80 °C
  作者：Dániel Eszenyi、Viktor Kelemen、Fanny Balogh、Miklós Bege、Magdolna Csávás、Pál Herczegh、Anikó Borbás

  DOI：10.1002/chem.201800668

  日期：2018.3.26

  The photoinitiated thiol‐ene coupling reactions of 2‐substituted glycals were studied as a generally applicable strategy for stereoselective 1,2‐cis‐α‐thioconjugation. Although all glycals reacted with full α‐selectivity, the efficacy of the reactions varied in a broad range depending on their configuration and glycals bearing axial acetoxy substituents reacted with very low efficacy at room temperature

  研究了2-取代的糖的光引发硫醇-烯偶联反应，作为立体选择性的1,2-顺-α-硫缀合的普遍适用策略。尽管所有糖类均以完全的α-选择性反应，但反应的效率在很大程度上取决于其构型，带有轴向乙酰氧基取代基的糖类在室温下的反应效率很低。研究表明，冷却可促进反应进程，而加热则可抑制反应进程。在-80°C下，噻吩基向烯烃的快速可逆加成平衡几乎完全移向产物，从而导致有效的加成反应。通过利用这种独特的温度效应的一系列α硫代的升-fucosides， - d-半乳糖苷和d- GlcNAc衍生物的制备具有很高的功效和完全的立体选择性。
• HANESSIAN, STEPHEN;FAUCHER, ANNE-MARIE;LEGER, SERGE, TETRAHEDRON, 46,(1990) N, C. 231-243
  作者：HANESSIAN, STEPHEN、FAUCHER, ANNE-MARIE、LEGER, SERGE

  DOI：——

  日期：——