2,3,4,6-tetra-O-benzyl-1-O-trityl-D-glucitol | 14233-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-1-O-trityl-D-glucitol
• 英文别名: 2,3,4,6-O-tetrabenzyl-1-O-trityl-D-glucitol
• CAS: 14233-49-9
• 化学式: C₅₃H₅₂O₆
• 分子量: 784.992
• InChiKey: MLPIPMLNTHBKQQ-HRHVFIINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.33
• 重原子数：
  59.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-O-trityl-D-glucitol 在 nicotinium dichromate 、 盐酸羟胺 作用下， 以 吡啶 、 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 1,3,4,5-tetra-O-benzyl-6-O-trityl-L-sorbose oxime
  参考文献：
  名称：

  Synthesis and biological activity of acyclic anlogues of nojirimycin

  摘要：

  A series of acyclic compounds has been prepared which comprises compounds that mimic key structural elements of nojirimycin 1 and 1-deoxynojirimycin 2, both of which are highly effective glucosidase inhibitors, in order to ascertain if similar biological activity can be obtained with simpler structures. All of the compounds are competitive inhibitors of yeast alpha-glucosidase. with varying degrees of effectiveness, but none of them, in contrast to 1-deoxynojirimycin 2, show significant anti-HIV activity.

  DOI：

  10.1039/p19940002229
• 作为产物：
  描述：

  2,3,4,6-四-o-苄基-D-吡喃葡萄糖 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4,6-tetra-O-benzyl-1-O-trityl-D-glucitol
  参考文献：
  名称：

  Synthesis with partially benzylated sygars. X. New method for the synthesis of ketoses

  摘要：

  DOI：

  10.1021/jo01286a036

文献信息

• Chemical Synthesis of 1-Deoxy-<scp>L</scp>-fructose and<scp>L</scp>-Sorbose Through Carbonyl Translocation
  作者：Hsin-Pei Wu、Nai-Yun Hsu、Tai-Ni Lu、Che-Chien Chang

  DOI：10.1002/ejoc.201403196

  日期：2015.1

  Two rare sugars – 1-deoxy-L-fructose and L-sorbose – were synthesized from inexpensive starting materials by a carbonyl translocation method developed in our laboratory. Reduction of a known starting compound gave a 1,5-diol derivative. Selective protection of the corresponding primary alcohol and oxidation of the secondary alcohol provided the desired product in acyclic, protected form. Subsequent

  两种稀有糖——1-脱氧-L-果糖和L-山梨糖——是通过我们实验室开发的羰基易位方法从廉价的起始材料合成的。已知起始化合物的还原得到1,5-二醇衍生物。相应伯醇的选择性保护和仲醇的氧化提供了无环、受保护形式的所需产物。随后的脱保护导致从已知原料分五个步骤生产 1-脱氧-L-果糖，总产率为 42%。这种方法代表了 1-脱氧-L-果糖的化学合成的第一份报告。应用类似的策略将廉价的 D-葡萄糖转化为 L-山梨糖，L-山梨糖由已知起始材料分五步制备，总产率为 55%。
• Stereospecific cyclization to form C-furanosides
  作者：Bing-Hui Yang、Ji-Qing Jiang、Kan Ma、Hou-Ming Wu

  DOI：10.1016/0040-4039(95)00413-7

  日期：1995.4

  A cyclization of benzyl ethers with Sn2 active site at γ-position to form C-furanoside was studied.

  研究了在γ位具有S n 2活性位的苄基醚的环化反应，形成C-呋喃糖苷。
• Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose
  作者：Ian Cumpstey、Sebastian Gehrke、Sayeh Erfan、Riccardo Cribiu

  DOI：10.1016/j.carres.2008.04.010

  日期：2008.7

  Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either D-glucose or L-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.

  从D-葡萄糖或L-山梨糖开始，并采用闭环复分解作为关键步骤，报道了两种合成途径形成瓦伦胺的碳环前体。据报道1-表戊烯胺的低产率合成。讨论了基于氮的早期引入而从第三种可能的方法流向缬草胺的结果。