methyl 2,4-di-O-acetyl-α-L-rhamnopyranoside | 172163-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-acetyl-α-L-rhamnopyranoside
• 英文别名: methyl 2,4-di-O-acetyl-β-L-rhamnopyranoside；[(2S,3R,4R,5R,6S)-5-acetyloxy-4-hydroxy-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 172163-92-7
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: XJLYOSBECHLIKF-KNIGECSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 methyl 2,4-di-O-acetyl-α-L-rhamnopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到methyl 2,4-di-O-acetyl-3-O-trifluoromethanesulfonyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018
• 作为产物：
  描述：

  L-rhamnose hydrate 在 吡啶 、 ammonium cerium(IV) nitrate 、 二正丁基氧化锡 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 methyl 2,4-di-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018

文献信息

• Bashir, Nazir B.; Phythian, Sara J.; Reason, Andrew J., Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2203 - 2222
  作者：Bashir, Nazir B.、Phythian, Sara J.、Reason, Andrew J.、Roberts, Stanley M.

  DOI：——

  日期：——