methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-2-C-methyl-α-D-glucopyranoside | 132602-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-2-C-methyl-α-D-glucopyranoside
• 英文别名: [(2S,3S,4S,5R,6S)-2-(bromomethyl)-4,5,6-trimethoxy-5-methyloxan-3-yl] benzoate
• CAS: 132602-73-4
• 化学式: C₁₇H₂₃BrO₆
• 分子量: 403.27
• InChiKey: QZYMRFJCBRHWDH-BIYBGRMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-2-C-methyl-α-D-glucopyranoside 在 4 A molecular sieve 、 mercury(II) diacetate 、 四丁基碘化铵 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 水 、 丙酮 为溶剂， 生成 Benzoic acid (1S,2S,3S,4R)-4-hydroxy-2,3-dimethoxy-3-methyl-6-oxo-cyclohexyl ester
  参考文献：
  名称：

  Synthesis of Methyl-branched 2,3,4,5-Tetrahydroxycyclohexanone Derivatives via 6-Deoxyhex-5-enopyranosides

  摘要：

  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.

  DOI：

  10.1246/cl.1991.17

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。
• SATO, KEN-ICHI;SAKUMA, SHOGO;NAKAMURA, YUTAKA;YOSHIMURA, JUJI;HASHIMOTO, +, CHEM. LETT.,(1991) N, C. 17-20
  作者：SATO, KEN-ICHI、SAKUMA, SHOGO、NAKAMURA, YUTAKA、YOSHIMURA, JUJI、HASHIMOTO, +

  DOI：——

  日期：——