2,3,4,6-tetra-O-acetyl-ξ-D-talopyranosyl bromide | 114028-03-4

• 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: 2,3,4,6-tetra-O-acetyl-ξ-D-talopyranosyl bromide
• CAS: 114028-03-4
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: CYAYKKUWALRRPA-XHVMDGRWSA-N

物化性质

• 熔点：
  84-84.5 °C
• 沸点：
  412.0±45.0 °C(predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-ξ-D-talopyranosyl bromide 在 甲醇 、 无水碳酸镉 、 氨 作用下， 以 硝基甲烷 为溶剂， 反应 24.17h， 生成 9-Hydroxy-5,11-dimethyl-2-((2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-6H-pyrido[4,3-b]carbazol-2-ium; bromide
  参考文献：
  名称：

  Synthesis and antitumor activity of quaternary ellipticine glycosides, a series of novel and highly active antitumor agents

  摘要：

  A series of ellipticine glycosides [2-N-glycosyl quaternary pyridinium salts of three ellipticines: ellipticine (1), 9-methoxyellipticine (2), and 9-hydroxyellipticine (4)] were stereoselectively synthesized in good yields by an improved condensation reaction between ellipticines [1, 2, and 9-acetoxyellipticine (3)] and protected (peracylated and perbenzylated) glycosyl halides with cadmium carbonate, followed by deprotection. These glycosides were preliminarily evaluated for their antitumor activity in the L1210 leukemia system. Twenty-six (53%) of the 49 glycosides tested were curative, and five [9-hydroxyellipticine L-arabinopyranoside (41b), D-lyxofuranoside (43a), L-lyxopyranoside (44b), D-xylofuranoside (49a), and L-rhamnopyranoside (56)] were selected for extended evaluation on the basis of their high levels of activity. The structure-activity relationships are discussed. The selected glycosides showed remarkable activity in six different murine tumor systems with excellent therapeutic ratios; their efficacy surpassed that of doxorubicin against three of these systems. On the basis of these results and ease of formulation, the two glycosides 41b (SUN4599) and 49a (SUN5073) were selected for further preclinical evaluation and possible clinical development.

  DOI：

  10.1021/jm00402a007

文献信息

• Efficient Synthesis of Glycosylated Asparaginic Acid Building Blocks via Click Chemistry
  作者：Thomas Ziegler、Nikolas Pietrzik、Carsten Schips

  DOI：10.1055/s-2008-1032150

  日期：2008.2

  4-tri- O-acetyl-6-azido-6-deoxy-1-thioglycosides (gluco, galacto, manno series), respectively (click chemistry). Thus obtained orthogonally protected L-asparaginic and ( S)-3-aminobutyric acids bearing an acetyl-protected glycose or glycoside moiety, linked through a triazole spacer, are suitable building blocks for combinatorial glycopeptide syntheses.

  铜催化 1完全乙酰化的炔丙基 1-硫糖苷（葡萄糖、半乳糖、甘露糖和鼠李糖系列）和 Fmoc-L-Asp(O-T-Bu)炔丙基酰胺与叔丁基 (S)-4-azido-3 的 ,3-偶极环加成-芴基甲氧基氨基丁酸、2,3,4,6-三-O-乙酰-糖基叠氮化物和乙基 2,3,4-三-O-乙酰-6-叠氮基-6-脱氧-1-硫糖苷（葡萄糖、半乳糖、甘露糖）系列），分别（点击化学）。由此获得的正交保护的L-天冬酰胺酸和(S)-3-氨基丁酸带有乙酰基保护的糖或糖苷部分，通过三唑间隔物连接，是组合糖肽合成的合适构件。
• Diastereoselective synthesis of C-glycosylphosphonates via free-radical glycosylation
  作者：Hans-Dieter Junker、Wolf-Dieter Fessner

  DOI：10.1016/s0040-4039(97)10498-1

  日期：1998.1

  A single step approach for the diastereoselective synthesis of C-glycosidic sugar phosphonates was developed by utilizing a free radical coupling to dialkyl vinylphosphonates to give the title compounds in moderate yield. The method is broadly applicable to sugars, deoxysugars, aminosugars, and oligosaccharides. (C) 1997 Elsevier Science Ltd. All rights reserved.