methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside | 65947-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside
• 英文别名: [(1S,2S,4S,5S,6S)-4-(bromomethyl)-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-yl] benzoate
• CAS: 65947-60-6
• 化学式: C₁₄H₁₅BrO₅
• 分子量: 343.174
• InChiKey: YHKKZHFZCBFUSU-JLDUMIBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside 在 tetrabutylammonium borohydride 作用下， 以 苯 为溶剂， 以59%的产率得到Benzoic acid (1S,2S,4R,5R,6S)-2-methoxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
  参考文献：
  名称：

  An Efficient Deoxysugar Synthesis using Bu₄NBH₄via an S_N2 Reduction

  摘要：

  脱氧糖衍生物由相应的三酸酯、对甲苯磺酸盐、卤素和环氧化物衍生物制备而成。利用四丁基四氢硼酸铵试剂，脱氧反应通过 SN2 型置换进行，收率很高。

  DOI：

  10.1246/cl.1992.1469

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。