methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-3-C-methyl-α-D-glucopyranoside | 132602-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-3-C-methyl-α-D-glucopyranoside
• CAS: 132602-79-0
• 化学式: C₁₉H₂₃BrO₈
• 分子量: 459.291
• InChiKey: ZBQKNAVTKMHLJG-SMYFESCOSA-N

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-3-C-methyl-α-D-glucopyranoside 在 sodium cyanoborohydride 作用下， 以 六甲基磷酰三胺 为溶剂， 以86%的产率得到methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-3-C-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  几种支链 6-Deoxyhex-5-enopyranosides 催化氢化中的立体选择性。支链甲基 6-Deoxy-β-L-hexopyranoside 的合成

  摘要：

  在钯碳存在的情况下，几种 2-C、3-C 和 4-C-甲基支链的 6-脱氧己-5-烯吡喃糖苷在乙醇中的氢化反应显示出相应的 6-脱氧-β-L-吡喃己糖苷的立体选择性形成.

  DOI：

  10.1246/bcsj.65.292

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。
• Synthesis of Methyl-branched 2,3,4,5-Tetrahydroxycyclohexanone Derivatives via 6-Deoxyhex-5-enopyranosides
  作者：Ken-ichi Sato、Shogo Sakuma、Yutaka Nakamura、Juji Yoshimura、Hironobu Hashimoto

  DOI：10.1246/cl.1991.17

  日期：1991.1

  Seven novel methyl-branched 2,3,4,5-tetrahydroxycyclohexanone derivatives were prepared in good yields by Ferrier reaction via corresponding key intermediates: 6-deoxyhex-5-enopyranosides.