2,3,4,5,6-penta-O-benzyl-scyllo-inosose | 106600-11-7

• 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: 2,3,4,5,6-penta-O-benzyl-scyllo-inosose
• 英文别名: 1,3,4,5,6-Pentakisbenzoylmyoinosose-2；2r,3t,4c,5t,6c-pentakis-benzoyloxy-cyclohexanone；2r,3t,4c,5t,6c-Pentakis-benzoyloxy-cyclohexanon；2-Oxo-penta-O-benzoyl-2-desoxy-myo-inosit；Penta-O-benzoyl-myo-inosose-(2)；Penta-O-benzoyl-scyllo-inosose
• CAS: 106600-11-7
• 化学式: C₄₁H₃₀O₁₁
• 分子量: 698.683
• InChiKey: WPDGSVLGLGWXEE-QNMOFYLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  52.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  148.57
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6-penta-O-benzyl-scyllo-inosose 在 sodium acetate 、 溶剂黄146 作用下， 生成 2,3,5-Tris-benzoyloxy-phenol
  参考文献：
  名称：

  Reflections on Dobermanns, poodles, and social rehabilitation for difficult-to-serve individuals with traumatic brain injury

  摘要：

  DOI：

  10.1080/026870300401432
• 作为产物：
  描述：

  1,3,4,5,6-Pentakisbenzoylmyoinositol 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 以90%的产率得到2,3,4,5,6-penta-O-benzyl-scyllo-inosose
  参考文献：
  名称：

  The Oxidation of Partially Acylated Myoinositols

  摘要：

  摘要：通过对肌醇进行受控催化酰化，得到了1,3,4,6-四酰和1,3,4,5,6-五酰肌醇。取代程度取决于反应条件和酰化试剂的结构，包括立体因素。铬酸氧化将酰肌醇转化为相应的2-酮。在电子轰击下，这些化合物经历逐步去酰化。

  DOI：

  10.1515/znb-1996-0114

文献信息

• Stereochemical Recognition of Doubly Functional Aminotransferase in 2-Deoxystreptamine Biosynthesis
  作者：Kenichi Yokoyama、Fumitaka Kudo、Mieko Kuwahara、Kousuke Inomata、Hideyuki Tamegai、Tadashi Eguchi、Katsumi Kakinuma

  DOI：10.1021/ja0445948

  日期：2005.4.1

  The doubly functional aminotransferase BtrS in the 2-deoxystreptamine (DOS) biosynthesis, in which two transaminations are involved, was characterized by a genetic as well as a chemical approach with the heterologously expressed enzyme. The gene disruption study clearly showed that BtrS is involved, in addition to the previously confirmed first transamination, in the second transamination as well. This dual function of BtrS for the DOS biosynthesis was further confirmed by the structural determination of the reverse reaction product from DOS. Enantiospecific formation of the reverse reaction product from DOS clearly showed that BtrS distinguishes the enantiotopic amino groups of DOS, but in contrast, both enantiomers of 2-deoxy-scyllo-inosose (DOI) were efficiently accepted by BtrS to give a racemic product. This unique stereochemical recognition of DOI chirality and DOS prochirality by BtrS is mechanistically explained by a specific hydrogen-bond donating force in the enzyme active site as a particular feature of this doubly functional enzyme.
• Synthesis of Some Substituted Cyclitols and Correlation of Structure with Their Spectra¹
  作者：N. Z. STANACEV、M. KATES

  DOI：10.1021/jo01062a066

  日期：1961.3