tri-O-acetyl-α-D-lyxopyranosyl chloride | 32445-42-4

• 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: tri-O-acetyl-α-D-lyxopyranosyl chloride
• 英文别名: 2,3,4-Tri-O-acetyl-α-D-lyxopyranosylchlorid；[(3R,4S,5S,6R)-4,5-diacetyloxy-6-chlorooxan-3-yl] acetate
• CAS: 32445-42-4
• 化学式: C₁₁H₁₅ClO₇
• 分子量: 294.689
• InChiKey: JWDUFIUUDGFMTM-RCWTZXSCSA-N

物化性质

• 沸点：
  330.8±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  tri-O-acetyl-α-D-lyxopyranosyl chloride 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-((2R,3S,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-6H-pyrido[4,3-b]carbazol-2-ium; chloride
  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
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-α-D-lyxopyranose 在 氯仿 、 四氯化钛 作用下， 生成 tri-O-acetyl-α-D-lyxopyranosyl chloride
  参考文献：
  名称：

  Zinner; Brandner, Chemische Berichte, 1956, vol. 89, p. 1507,1514

  摘要：

  DOI：

文献信息

• Stereoselective Preparation of <i>C</i> ‐Aryl Glycosides <i>via</i> Visible‐Light‐Induced Nickel‐Catalyzed Reductive Cross‐Coupling of Glycosyl Chlorides and Aryl Bromides
  作者：Ze‐Dong Mou、Jia‐Xi Wang、Xia Zhang、Dawen Niu

  DOI：10.1002/adsc.202100343

  日期：2021.6.21

  A nickel-catalyzed cross-coupling reaction of glycosyl chlorides with aryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the use of bench-stable glycosyl chlorides, allowing the highly stereoselective synthesis of C-aryl glycosides.

  已经开发了一种镍催化的糖基氯与芳基溴的交叉偶联反应。该反应在可见光照射下顺利进行，并使用了实验室稳定的糖基氯，可以高度立体选择性地合成C-芳基糖苷。
• Darstellung und Konformation der 1,2-cis-Pentopyranosylazide
  作者：Zoltán Györgydeák、László Szilágyi

  DOI：10.1002/jlac.198619860810

  日期：1986.8.15

  Die Umsetzung der acetylierten 1,2-trans-Pentopyranosylhalogenide 1a, b, 2, 3 mit NaN3 in HMPT unter milden Bedingungen ergibt die 4 möglichen 1,2-cis-2,3,4-Tri-O-acetylpentopyranosylazide 4, 6, 8 und 14, die durch Entacetylierung in die freien Azide 5, 7, 9 und 15 übergeführt werden. Anhand der vicinalen Proton-Proton-Kopplungskonstanten werden die 4C1(D)⇌1C4(D)-Konformationsgleichgewichte in Lösung

  在温和条件下，乙酰化的1,2-反式-戊吡喃糖基卤化物1a，b，2、3与NaN 3在温和条件下的反应产生了4种可能的1,2-顺式-2,3,4-三-O-乙酰基戊吡喃糖基叠氮化物4，6，8和14，其被转化成游离的叠氮化物5，7，9和15通过脱乙酰化。基于邻位质子-质子偶合常数时，4 Ç 1（d）⇌ 1 Ç 4（d）的构象平衡在溶液中讨论，并与相关的吡喃糖衍生物相比较。