1,3,4,6-Tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-deoxy-β-D-glucopyranose | 23345-61-1

• 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: 1,3,4,6-Tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-deoxy-β-D-glucopyranose
• CAS: 23345-61-1
• 化学式: C₂₄H₃₂O₁₄
• 分子量: 544.51
• InChiKey: GYHDLQWHVHJGME-BPIZVXQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  176.26
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-Tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-deoxy-β-D-glucopyranose 在 hydrogenation catalyst 氢气 作用下， 以 苯 为溶剂， 以89%的产率得到1,3,4,6-Tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranosyl)-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Wessel, Hans Peter; Englert, Gerhard, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 2, p. 179 - 196

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 三氟化硼 作用下， 生成 1,3,4,6-Tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  CH-Deprotonation mediated by a remote syn-axial acetoxy group—an unprecedented double bond formation upon cyanation of the dimer from l-fucal

  摘要：

  Replacement of the anomeric acetate by a cyanide group in the dimer of di-O-acetyl-L-fucal by the action of mild Lewis acid [Hg(CN)(2)-HgBr2-Me3SiCN], resulted not only in the desired transformation but also in the introduction of an additional double bond between C-2A and C-3A. Due to its configuration, the remote C-4A acetoxy group may facilitate the deprotonation by functioning as an internal base. H-1 NMR spectroscopy and X-ray crystallography indicate that the conformations of both rings A and B and their relative orientation in the resulting C-linked disaccharidic glycosyl cyanide, 4-O-acetyl-2-C-(4-O-acetyl-2,3-dideoxy-alpha-L-threo-hex-2-enopyranosyl)-2,3-dideoxy-2-enO-alpha-L-fucopyranosl cyanide, in solution are virtually identical to the crystal structure. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00048-x