5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose | 876935-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose
• 英文别名: (2R,3S,4S)-4-[(2S)-oxiran-2-yl]-2,3,4-tris(phenylmethoxy)butanal
• CAS: 876935-54-5
• 化学式: C₂₇H₂₈O₅
• 分子量: 432.516
• InChiKey: OVMANRDORDPLFI-NFGXINMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose 、 (3-methyl-but-3-en-1-ynyl)-lithium 在 zinc(II) chloride 、 lithium bromide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 24.75h， 以73%的产率得到1-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-2-isoprenylacetylene
  参考文献：
  名称：

  Selective Synthesis of α-C-(Alkynyl)-galactosides by an Efficient Tandem Reaction

  摘要：

  Several alpha-C-(alkynyl)-galacto sides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.

  DOI：

  10.1021/jo0519817
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-galactose diethyldithioacetal 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 碘 、 calcium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 5,6-anhydro-2,3,4-tri-O-benzyl-L-altro-hexose
  参考文献：
  名称：

  Selective Synthesis of α-C-(Alkynyl)-galactosides by an Efficient Tandem Reaction

  摘要：

  Several alpha-C-(alkynyl)-galacto sides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.

  DOI：

  10.1021/jo0519817

文献信息

• Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000
  作者：Aline Banchet-Cadeddu、Agathe Martinez、Stéphane Guillarme、Véronique Parietti、Fanny Monneaux、Eric Hénon、Jean-Hugues Renault、Jean-Marc Nuzillard、Arnaud Haudrechy

  DOI：10.1016/j.bmcl.2011.02.044

  日期：2011.4

  Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening (the NEO strategy). Through the use of a common pivotal structure, a new C-galactoside ester analogue (23) was synthesized which showed an encouraging T(H)2 biased response during preliminary biological tests. (C) 2011 Elsevier Ltd. All rights reserved.
• Selective Synthesis of α-<i>C</i>-(Alkynyl)-galactosides by an Efficient Tandem Reaction
  作者：Stéphane Guillarme、Karen Plé、Arnaud Haudrechy

  DOI：10.1021/jo0519817

  日期：2006.2.1

  Several alpha-C-(alkynyl)-galacto sides were synthesized using a tandem reaction involving the addition of a metal alkynylide to a chiral acyclic epoxyaldehyde, followed by an in situ closure of the generated alkoxide on the epoxide function.