acetyl 2,4-di-O-acetyl-D-xylopyranoside | 170555-82-5

• 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: acetyl 2,4-di-O-acetyl-D-xylopyranoside
• 英文别名: 1,2,4-tri-O-acetyl-D-xylopyranose；[(3R,4S,5R)-5,6-diacetyloxy-4-hydroxyoxan-3-yl] acetate
• CAS: 170555-82-5
• 化学式: C₁₁H₁₆O₈
• 分子量: 276.243
• InChiKey: YTFFSUDKQYXXIY-GZBOUJLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  acetyl 2,4-di-O-acetyl-D-xylopyranoside 在 氢氧化钾 、 三氟化硼乙醚 、 silver perchlorate 、 四氯化锡 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 1.33h， 生成
  参考文献：
  名称：

  Stereocontrolled Elaboration of Natural (−)-Polycavernoside A, a Powerfully Toxic Metabolite of the Red Alga Polycavernosa tsudai

  摘要：

  A stereoselective total synthesis of natural levorotatory polycavemoside A (1) has been achieved. initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. This objective was followed by preparation of the phenylsulfonyl-substituted tetrahydropyran 23 and aldehyde 30. After proper linking of these key compounds, important information had to be garnered on the sequence of steps that would ultimately result in successful access to 1. Although oxidation to generate alpha-diketone 35 and unmasking of the C-13 hydroxyl did give rise efficiently to lactol 36, this functionality did not pave the way for ensuring macrolactonization. When this sequence of steps was reversed, it was indeed possible to arrive at the heavily functionalized precursor 43. However, numerous experiments failed to result in the requisite activation of C-16 for attachment of the trienyl side chain. However, if the E-vinyl iodide was elaborated in advance of alpha-diketone generation, glycosidation, and complete side chain construction, arrival at 1 proceeded without unsurmountable complications to furnish the targeted marine toxin.

  DOI：

  10.1021/ja993487o
• 作为产物：
  描述：

  1,2,4-tri-O-acetyl-3-O-benzyl-α,β-D-xylopyranose 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以97%的产率得到acetyl 2,4-di-O-acetyl-D-xylopyranoside
  参考文献：
  名称：

  针对聚卡维诺糖苷A的全合成的研究。二糖成分的对映选择性合成

  摘要：

  Mukaiyama-Nicolaou规程适应单未保护的硫代糖苷与糖基氟化物的偶联能够递送标题毒素中存在的异常二糖。

  DOI：

  10.1016/0040-4039(95)00789-f

文献信息

• Efficient and selective removal of chloroacetyl group promoted with tetra-n-butylammonium fluoride (TBAF)
  作者：Guofeng Gu、Min Fang、Yuguo Du

  DOI：10.1016/j.carres.2011.09.033

  日期：2011.12

  A practical method for the efficient and selective cleavage of chloroacetyl protecting group using tetra-n-butylammonium fluoride (TBAF) in THF solution at rt was disclosed.

  公开了在室温下使用四正丁基氟化铵（TBAF）在THF溶液中有效和选择性地裂解氯乙酰基保护基团的实用方法。
• Synthesis of a tetrasaccharide related to the triterpenoid saponin Bellisoside isolated from Bellis perennis (compositae)
  作者：Santanu Mandal、Nayan Sharma、Balaram Mukhopadhyay

  DOI：10.1016/j.tetasy.2010.06.032

  日期：2010.9

  A concise synthesis of a tetrasaccharide related to the triterpenoid saponins Bellisoside has been accomplished from commercially available monosaccharides through rational protecting group manipulations and stereoselective glycosylations. For the glycosylation reactions, H2SO4–silica has been successfully used as an alternative to conventional Lewis acids such as TfOH or TMSOTf. The target tetrasaccharide

  已经通过合理的保护基团操作和立体选择性糖基化作用，从市售单糖中完成了与三萜皂苷甜菊苷相关的四糖的简明合成。对于糖基化反应，H 2 SO 4-二氧化硅已成功用作传统路易斯酸（例如TfOH或TMSOTf）的替代物。靶四糖已经以其对-甲氧基苯基糖苷的形式合成，通过对-甲氧基苯基糖苷的选择性脱保护，然后进行三氯乙亚氨酸化学反应，为进一步的糖缀合物形成留有空间。