Acetic acid (2R,3R,4R,6R)-3-acetoxy-6-iodo-2-methyl-tetrahydro-pyran-4-yl ester | 634584-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,6R)-3-acetoxy-6-iodo-2-methyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,6R)-3-acetyloxy-6-iodo-2-methyloxan-4-yl] acetate
• CAS: 634584-50-2
• 化学式: C₁₀H₁₅IO₅
• 分子量: 342.131
• InChiKey: PPFPIBLGKKNLQH-STRWAFKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  邻甲酚 、 Acetic acid (2R,3R,4R,6R)-3-acetoxy-6-iodo-2-methyl-tetrahydro-pyran-4-yl ester 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以42%的产率得到o-cresyl 3,4-di-O-acetyl-2,6-dideoxy-β-D-lyxo-pyranoside
  参考文献：
  名称：

  Recent advances in the synthesis of 2-deoxy-glycosides

  摘要：

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.07.013
• 作为产物：
  描述：

  1,3,4-Tri-O-acetyl-2,6-didesoxy-D-arabino-hexopyranose 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 Acetic acid (2R,3R,4R,6R)-3-acetoxy-6-iodo-2-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Landomycin D的合成：糖精组装的研究

  摘要：

  摘要 描述了土地霉素D（土地霉素的二糖同系物）的合成，详细介绍了将2-脱氧糖单元组装到安古环素糖苷配基上的过程。 描述了土地霉素D（土地霉素的二糖同系物）的合成，详细介绍了将2-脱氧糖单元组装到安古环素糖苷配基上的过程。

  DOI：

  10.1055/s-0035-1561949

文献信息

• Efficient Route to 2-Deoxy β-<i>O</i>-Aryl-<scp>d</scp>-Glycosides via Direct Displacement of Glycosyl Iodides
  作者：Son N. Lam、Jacquelyn Gervay-Hague

  DOI：10.1021/ol035705v

  日期：2003.10.1

  The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-beta-O-aryl glycosides. Direct displacement of the anomeric iodide alleviates the need to introduce temporary C-2 stereodirecting groups that require subsequent removal. The only observable byproducts from the glycosylations result from elimination of HI giving the starting glycals, which can be recycled through the reaction sequence.