methyl 2,3,4-tri-O-acetyl-α-D-lyxopyranoside | 32445-37-7

• 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-acetyl-α-D-lyxopyranoside
• 英文别名: methyl 2,3,4-acetyl-α-D-lyxopyranoside；Methyl-(tri-O-acetyl-α-D-lyxopyranosid)；Methyl-β-D-lyxopyranosid-triacetat；methyl-(tri-O-acetyl-α-D-lyxopyranoside)；[(3R,4S,5S,6S)-4,5-diacetyloxy-6-methoxyoxan-3-yl] acetate
• CAS: 32445-37-7
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: YBESHGJFPWHRBW-RHYQMDGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-D-lyxopyranoside 在 吡啶 、 甲醇 、 三氟甲磺酸酐 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 29.5h， 生成 methyl 2,3-O-cyclohexylidene-4-deoxy-4-azido-β-L-ribopyranoside
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

  摘要：

  A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-alpha-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.

  DOI：

  10.1021/np4003096
• 作为产物：
  描述：

  D-lyxose 在 吡啶 、 乙酰氯 作用下， 生成 methyl 2,3,4-tri-O-acetyl-α-D-lyxopyranoside
  参考文献：
  名称：

  McGeary, Ross P.; Rasoul Amini, Sara; Tang, Vincent W. S., Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2727 - 2730

  摘要：

  DOI：

文献信息

• Levene; Wolfrom, Journal of Biological Chemistry, 1928, vol. 78, p. 525,532
  作者：Levene、Wolfrom

  DOI：——

  日期：——
• RELATIONS BETWEEN ROTATORY POWER AND STRUCTURE IN THE SUGAR GROUP. XVIII. ALPHA-METHYL d-LYXOSIDE TRIACETATE^1,2
  作者：F. P. Phelps、C. S. Hudson

  DOI：10.1021/ja01394a044

  日期：1928.7