methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(3-phenylprop-2-enyl)-D-erythro-L-gluco-nonoate | 1045795-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(3-phenylprop-2-enyl)-D-erythro-L-gluco-nonoate
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(E)-3-phenylprop-2-enyl]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1045795-17-2
• 化学式: C₂₉H₃₇NO₁₂
• 分子量: 591.612
• InChiKey: AYKYUIHPNTVCRQ-NYNGGBRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(3-phenylprop-2-enyl)-D-erythro-L-gluco-nonoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Cross metathesis for the synthesis of novel C-sialosides

  摘要：

  Cross metathesis of both anomers of C-allyl sialoside (3 alpha/3 beta) with styrene catalyzed by the second generation Grubbs or Hoveyda-Grubbs catalysts gave the corresponding aryl derivatives (4 alpha/4 beta) in virtually quantitative yields. The products were hydrogenated to model compounds 5 alpha/5 beta. Similarly, reaction of the alpha-anomer 3 alpha with galactose derivative 8 gave the olefin-linked disaccharide mimetic 9. Following hydrogenation and deprotection, the ethylene-bridged Neu5Ac alpha(2 -> 6)Gal analogue 11 could be obtained. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.036
• 作为产物：
  描述：

  苯乙烯 、 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-gluco-nononate 在 second generation Grubbs catalyst (ruthenium comp.) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-(3-phenylprop-2-enyl)-D-erythro-L-gluco-nonoate
  参考文献：
  名称：

  Cross metathesis for the synthesis of novel C-sialosides

  摘要：

  Cross metathesis of both anomers of C-allyl sialoside (3 alpha/3 beta) with styrene catalyzed by the second generation Grubbs or Hoveyda-Grubbs catalysts gave the corresponding aryl derivatives (4 alpha/4 beta) in virtually quantitative yields. The products were hydrogenated to model compounds 5 alpha/5 beta. Similarly, reaction of the alpha-anomer 3 alpha with galactose derivative 8 gave the olefin-linked disaccharide mimetic 9. Following hydrogenation and deprotection, the ethylene-bridged Neu5Ac alpha(2 -> 6)Gal analogue 11 could be obtained. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.036