(2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-prop-2-enyloxane | 952312-34-4

• 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: (2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-prop-2-enyloxane
• CAS: 952312-34-4
• 化学式: C₃₀H₃₄O₄
• 分子量: 458.598
• InChiKey: WBMQTRIOEYMRSN-WQJDAVBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-prop-2-enyloxane 、 methyl acryloyl-L-leucyl-L-alanyl-L-prolinate 在 substituted Grubbs-type ruthenium carbene complex 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以53%的产率得到methyl (2S)-1-[(2S)-2-[[(2S)-4-methyl-2-[[(E)-4-[(2R,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]but-2-enoyl]amino]pentanoyl]amino]propanoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Cross‐metathesis ofC‐Glycosides and Peptides

  摘要：

  Peptides bearing an acryloyl residue at their N-terminus were coupled with various C-glycosides in an equimolar ratio via cross-metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerization of the starting materials. The posttranslational cross-metathesis approach was shown to be suitable for the combinatorial synthesis of a small library of C-glycopeptides.

  DOI：

  10.1080/00397910701481146
• 作为产物：
  描述：

  烯丙基三丁基锡 、 phenyl 2,3,4-O-tri-benzyl-1-thio-β-L-fucopyranosyl sulfoxide 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-prop-2-enyloxane 、 3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene
  参考文献：
  名称：

  Studies on the Stereoselective Synthesis of C-Allyl Glycosides

  摘要：

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.

  DOI：

  10.1021/ol801710s

文献信息

• Cross‐metathesis of<i>C</i>‐Glycosides and Peptides
  作者：Peter Brüchner、David Koch、Ulrike Voigtmann、Siegfried Blechert

  DOI：10.1080/00397910701481146

  日期：2007.8

  Peptides bearing an acryloyl residue at their N-terminus were coupled with various C-glycosides in an equimolar ratio via cross-metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerization of the starting materials. The posttranslational cross-metathesis approach was shown to be suitable for the combinatorial synthesis of a small library of C-glycopeptides.
• Studies on the Stereoselective Synthesis of <i>C</i>-Allyl Glycosides
  作者：Glenn J. McGarvey、Christopher A. LeClair、Bahar A. Schmidtmann

  DOI：10.1021/ol801710s

  日期：2008.11.6

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.