methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-7-iodo-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside | 951011-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-7-iodo-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(2-iodoethynyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 951011-25-9
• 化学式: C₂₉H₂₉IO₅
• 分子量: 584.451
• InChiKey: SFIGDOTWJWJBAB-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-7-iodo-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside 在 indium 、 palladium on activated charcoal 甲醇 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl-2,3,4,11,13-penta-O-acetate-9,10-dideoxy-D-glycero-D-ido-α-D-glucotridecaopyranoside
  参考文献：
  名称：

  Ferrier-Type Alkynylation Reaction Mediated by Indium

  摘要：

  An efficient Ferrier-type alkynylation reaction between glycals and iodoalkynes using Barbier conditions is described. These conditions require In-0, In-I, or In-II and lead to alpha-2,3-unsaturated-C-glycosides with good stereoselectivity. When glycosyliodoalkynes are used, trehalose-derived compounds and alpha-(1 -> 6)-C-disaccharides are obtained.

  DOI：

  10.1021/ol701480x
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-ynopyranoside 在 吗啉 、 碘 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 以74%的产率得到methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-7-iodo-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside
  参考文献：
  名称：

  Ferrier-Type Alkynylation Reaction Mediated by Indium

  摘要：

  An efficient Ferrier-type alkynylation reaction between glycals and iodoalkynes using Barbier conditions is described. These conditions require In-0, In-I, or In-II and lead to alpha-2,3-unsaturated-C-glycosides with good stereoselectivity. When glycosyliodoalkynes are used, trehalose-derived compounds and alpha-(1 -> 6)-C-disaccharides are obtained.

  DOI：

  10.1021/ol701480x

文献信息

• Direct <i>C</i>-Glycosylation by Indium-Mediated Alkynylation on Sugar Anomeric Position
  作者：Nadège Lubin-Germain、Jean-Pierre Baltaze、Alexis Coste、Agnès Hallonet、Hugo Lauréano、Grégory Legrave、Jacques Uziel、Jacques Augé

  DOI：10.1021/ol7029257

  日期：2008.3.1

  Indium-mediated alkynylation reaction was studied for the direct preparation of C-glycosides. Easily available starting sugar derivatives with an acetyl group at the anomeric position were tested as electrophiles toward alkynylindium reagents under Barbier conditions. Good yields and stereoselectivities were observed during the reaction. The alkynylation was applied to the synthesis of an alpha-(1 -> 6)-C-disaccharide analogue of isomaltoside.