1,2,3,4-tetra-O-acetyl-6-deoxy-β-L-glucopyranose | 36807-81-5

• 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: 1,2,3,4-tetra-O-acetyl-6-deoxy-β-L-glucopyranose
• 英文别名: [(2S,3S,4R,5S,6R)-4,5,6-triacetyloxy-2-methyloxan-3-yl] acetate
• CAS: 36807-81-5
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: QZQMGQQOGJIDKJ-AAQSURGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Acetic acid (2S,3S,4S,5S)-4-acetoxy-5,6-dihydroxy-2-methyl-tetrahydro-pyran-3-yl ester 、 乙酸酐 在 吡啶 作用下， 生成 1,2,3,4-tetra-O-acetyl-6-deoxy-α-L-glucopyranose 、 1,2,3,4-tetra-O-acetyl-6-deoxy-β-L-glucopyranose
  参考文献：
  名称：

  An Efficient Stereoselective Dihydroxylation of Glycals using a Bimetallic System, RuCl₃/CeCl₃/NaIO₄

  摘要：

  A catalytic dihydroxylation reaction on glycals has been developed using a bimetallic oxidizing system to furnish sugar 1,2-diols in a highly setreoselective manner.

  DOI：

  10.1021/jo0526385

文献信息

• Manipulation of free carbohydrates via stannylene acetals. Preparation of β-per-O-acyl derivatives of d-mannose, l-rhamnose, 6-O-trityl-d-talose, and d-lyxose
  作者：György Hodosi、Pavol Kováč

  DOI：10.1016/s0008-6215(97)00155-9

  日期：1997.9

  Abstract A simple and high-yielding method for the preparation of 1- O - β -acyl derivatives of carbohydrates with an axial OH group at C-2 is described. It utilizes the property of unprotected carbohydrates to preferentially form 1,2- O - cis stannylene acetals, when treated with dibutyltin oxide. These acetals can be acylated with retention of configuration at the anomeric position.

  摘要描述了一种简单高效的方法，用于制备在C-2处带有轴向OH基的碳水化合物的1- O-β-酰基衍生物。当用二丁基氧化锡处理时，它利用未保护的碳水化合物的特性优先形成1,2-O-顺式亚锡缩醛。这些缩醛可以被酰化，并保持在异头位置的构型。
• An Efficient Stereoselective Dihydroxylation of Glycals using a Bimetallic System, RuCl₃/CeCl₃/NaIO₄
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1021/jo0526385

  日期：2006.3.31

  A catalytic dihydroxylation reaction on glycals has been developed using a bimetallic oxidizing system to furnish sugar 1,2-diols in a highly setreoselective manner.