methyl 3-O-acetyl-2,4-di-O-benzoyl-6-bromo-6-deoxy-α-D-altropyranoside | 120123-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-acetyl-2,4-di-O-benzoyl-6-bromo-6-deoxy-α-D-altropyranoside
• 英文别名: [(2S,3S,4R,5S,6S)-4-acetyloxy-5-benzoyloxy-2-(bromomethyl)-6-methoxyoxan-3-yl] benzoate
• CAS: 120123-45-7
• 化学式: C₂₃H₂₃BrO₈
• 分子量: 507.335
• InChiKey: WXKIGUURQQQMGT-PXUBBOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-2,4-di-O-benzoyl-6-bromo-6-deoxy-α-D-altropyranoside 生成 [(3S,4R,6S)-4-acetyloxy-6-methoxy-2-methylideneoxan-3-yl] 3-benzoyloxybenzoate
  参考文献：
  名称：

  SATO, KEN-ICHI;KUBO, N.;TAKADA, R.;HASHIMOTO, H.;YOSHIMURA, J., CHEM. LETT.,(1988) N 10, C. 1703-1704

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside 生成 methyl 3-O-acetyl-2,4-di-O-benzoyl-6-bromo-6-deoxy-α-D-altropyranoside
  参考文献：
  名称：

  AQEEL, AMJAD;SATO, KEN-ICHI;HASHIMOTO, HIRONOBU;YOSHIMURA, JUJI, J. CARBOHYDR. CHEM., 8,(1989) N, C. 405-412

  摘要：

  DOI：

文献信息

• Syntheses of 6-Deoxyhex-5-enopyranosides from 6-Bromo-6-deoxy- or 6-<i>O</i>-<i>p</i>-Tolylsulfonylhexopyranosides by the Use of DBU in DMSO
  作者：Ken-ichi Sato、Noriyuki Kubo、Ritsuko Takada、Shogo Sakuma

  DOI：10.1246/bcsj.66.1156

  日期：1993.4

  Various kinds of nonbranched and methyl-branched 6-deoxyhex-5-enopyranoside derivatives were prepared from 6-bromo-6-deoxy or 6-O-p-tolylsulfonylhexopyranoside in a one-pot procedure by a successive treatment with iodide anion and 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide. The scope and limitations of this reaction have become apparent by observing the reactions of 18 substrates. The yields of altropyranoside and 2-deoxyribo-hexopyranoside derivatives were high, except for the 2,3-anhydropyranoside derivative. Methyl-branched 6-deoxyhex-5-enopyranoside derivatives were also obtained in practical yields.

  各种非分支和甲基分支的6-脱氧己-5-烯吡喃苷衍生物是通过将6-溴-6-脱氧或6-O-对甲苯磺酰己吡喃苷与碘离子及1,8-二氮杂双环[5.4.0]十一烯在二甲基亚砜中进行连续处理，采用一锅法制备的。通过观察18种底物的反应，这一反应的范围和局限性变得明显。除了2,3-无水吡喃苷衍生物外，其他的反应产物（如altropyranoside和2-脱氧核糖己吡喃苷衍生物）产率较高。甲基分支的6-脱氧己-5-烯吡喃苷衍生物也以实用的产率获得。
• Convenient Synthesis of Hex-5-enopyranosides
  作者：Ken-ichi Sato、Noriyuki Kubo、Rituko Takada、Amjad Aqeel、Hironobu Hashimoto、Juji Yoshimura

  DOI：10.1246/cl.1988.1703

  日期：1988.10.5

  Hex-5-enopyranosides were prepared in an one-pot procedure from 6-bromo-6-deoxy- or 6-O-tosylhexopyranoside by the successive treatment with iodide anion and 1,8-diazabicyclo-[5.4.0]undec-7-ene in DMSO.

  通过在二甲基亚砜中连续处理碘离子和1,8-二氮杂双环[5.4.0]十一碳-7-烯，以一锅法从6-溴-6-脱氧-或6-O-对甲苯磺酰基己吡喃糖苷制备了六-5-烯吡喃糖苷。