methyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside | 195387-00-9

• 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: methyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside
• 英文别名: (2R,3S,4R,7R)-6-bromo-7-methoxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,7-tetrahydrooxepine
• CAS: 195387-00-9
• 化学式: C₂₉H₃₁BrO₅
• 分子量: 539.466
• InChiKey: XFWNFLULHRKBAU-OVHUPFAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-gulo-hexitol 在 silver(I) acetate 作用下， 反应 120.0h， 以11%的产率得到methyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-α-D-arabino-hept-2-enoseptanoside
  参考文献：
  名称：

  Synthesis of C-furanosides from ad-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence

  摘要：

  偕二溴环丙烷 1，由三-O-苄基-D-葡萄糖制备，在醇存在下经历热和银促进的环扩展，得到取代的氧杂环庚烷。随着进一步加热，环收缩成高度取代的四氢呋喃。这些代表 C-呋喃糖苷，可能用作 C-核苷和其他碳水化合物模拟物的前体。

  DOI：

  10.1039/c0cc02244f

文献信息

• Synthesis of Oxepines and 2-Branched Pyranosides from a <scp>d</scp>-Glucal-Derived <i>gem</i>-Dibromo-1,2-cyclopropanated Sugar
  作者：Russell J. Hewitt、Joanne E. Harvey

  DOI：10.1021/jo902306a

  日期：2010.2.5

  The conversion of cyclopropane-fused carbohydrates into oxepines is an attractive method for accessing diverse members of the septanoside family of carbohydrate mimetics. 2-Bromooxepines are obtained through silver(I)-promoted thermal ring expansion of a D-glucal-derived gem-dihalocyclopropanated sugar. In contrast, cyclopropane ring cleavage under basic conditions leads to 2-C-branched pyranosides, not the 2-bromooxepine structures assigned in an earlier report.
• Synthesis of C-furanosides from a<scp>d</scp>-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence
  作者：Russell J. Hewitt、Joanne E. Harvey

  DOI：10.1039/c0cc02244f

  日期：——

  gem-Dibromocyclopropane 1, prepared from tri-O-benzyl-D-glucal, undergoes thermal and silver-promoted ring expansion in the presence of alcohols to give substituted oxepines. With further heating, ring contraction to highly substituted tetrahydrofurans follows. These represent C-furanosides, potentially useful as precursors to C-nucleosides and other carbohydrate mimics.

  偕二溴环丙烷 1，由三-O-苄基-D-葡萄糖制备，在醇存在下经历热和银促进的环扩展，得到取代的氧杂环庚烷。随着进一步加热，环收缩成高度取代的四氢呋喃。这些代表 C-呋喃糖苷，可能用作 C-核苷和其他碳水化合物模拟物的前体。