tri-O-benzoyl-2-deoxy-β-L-erythro-pentopyranose | 192133-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tri-O-benzoyl-2-deoxy-β-L-erythro-pentopyranose
• 英文别名: [(2R,4R,5S)-2,5-dibenzoyloxyoxan-4-yl] benzoate
• CAS: 192133-19-0
• 化学式: C₂₆H₂₂O₇
• 分子量: 446.456
• InChiKey: HYQISMBJGQVBLA-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tri-O-benzoyl-2-deoxy-β-L-erythro-pentopyranose 生成 2-deoxy-L-ribose
  参考文献：
  名称：

  Efficient syntheses of l-ribose and 2-deoxy l-ribose from d-ribose and l-arabinose

  摘要：

  Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00870-8
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl bromide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以60%的产率得到tri-O-benzoyl-2-deoxy-β-L-erythro-pentopyranose
  参考文献：
  名称：

  Efficient syntheses of l-ribose and 2-deoxy l-ribose from d-ribose and l-arabinose

  摘要：

  Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00870-8

文献信息

• Deoxygenation of carbohydrates by thiol-catalysed radical-chain redox rearrangement of the derived benzylidene acetals
  作者：Hai-Shan Dang、Brian P. Roberts、Jasmeet Sekhon、Teika M. Smits

  DOI：10.1039/b212303g

  日期：2003.4.14

  efficient thiol-catalysed radical-chain redox rearrangement resulting in deoxygenation at one of the diol termini and formation of a benzoate ester function at the other. The role of the thiol is to act as a protic polarity-reversal catalyst to promote the overall abstraction of the acetal hydrogen atom by a nucleophilic alkyl radical. The redox rearrangement is carried out in refluxing octane and/or chlorobenzene

  衍生自碳水化合物中1,2-或1,3-二醇官能团的五元或六元环状亚苄基乙缩醛经过有效的硫醇催化的自由基链氧化还原重排，导致一个二醇末端的脱氧并形成一个苯甲酸酯的作用相反。硫醇的作用是充当质子极性反转催化剂，以促进亲核烷基自由基对乙缩醛氢原子的整体提取。氧化还原重排是在回流辛烷和/或氯苯作为溶剂的条件下进行的。温度为130摄氏度，由热分解二叔丁基过氧化物（DTBP）或2,2-双（叔丁基过氧）丁烷引发。硅烷硫醇（Bu（t）O）3SiSH和Pr（i）3SiSH（TIPST）是特别有效的催化剂，DTBP与TIPST结合使用通常是最有效和方便的组合。该反应已通过1，2-，3，4-和4，6-O-亚苄基吡喃糖酶和5，6-O-亚苄基呋喃糖用于各种单糖的单脱氧。它也已被用于引起甘露糖和二糖α，α-海藻糖的双脱氧。对甲氧基亚苄基乙缩醛的使用没有太大优势，并且在相似条件下，乙缩醛不会发生明显的氧化还原重排。官能团
• From a Carbohydrate Raw Material to an Important Building Block: Cost-Efficient Conversion of <scp>d</scp>-Fructose into 2-Deoxy-<scp>l</scp>-ribose
  作者：Ya-Han Hsu、Che-Chien Chang

  DOI：10.1021/acs.joc.2c01162

  日期：2022.10.7

  for the conversion of a low-cost carbohydrate (d-fructose) into an important carbohydrate building block (2-deoxy-l-ribose) is reported. This methodology involves a novel radical cyclization followed by a fragmentation reaction, selective enzymatic hydrolysis using a lipase, and oxidative cleavage of the vicinal diol. This method uses the cheapest starting material and employs the shortest synthetic

  报道了一种将低成本碳水化合物（d-果糖）转化为重要的碳水化合物结构单元（2-脱氧-l-核糖）的直接方法。该方法涉及一种新的自由基环化，然后是碎裂反应、使用脂肪酶的选择性酶水解和邻位二醇的氧化裂解。该方法使用最便宜的起始材料并采用最短的合成路线（7 步）将d-糖转化为 2-脱氧-l-核糖。
• Efficient syntheses of l-ribose and 2-deoxy l-ribose from d-ribose and l-arabinose
  作者：Michael E. Jung、Yue Xu

  DOI：10.1016/s0040-4039(97)00870-8

  日期：1997.6

  Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14. (C) 1997 Elsevier Science Ltd.
• Synthesis and Testing of New Modified Nucleosides
  作者：Michael E. Jung、Christopher J. Nichols、Oliver Kretschik、Yue Xu

  DOI：10.1080/15257779908041490

  日期：1999.4

  New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-e and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.