methyl 2,3-anhydro-4,6-di-O-benzoyl-α-D-allopyranoside | 112070-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-anhydro-4,6-di-O-benzoyl-α-D-allopyranoside
• 英文别名: [(1R,2S,4R,5R,6R)-5-benzoyloxy-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-4-yl]methyl benzoate
• CAS: 112070-63-0
• 化学式: C₂₁H₂₀O₇
• 分子量: 384.386
• InChiKey: KBIXCNPGFIQJFD-PLQGUWCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-allopyranoside 生成 methyl 2,3-anhydro-4,6-di-O-benzoyl-α-D-allopyranoside
  参考文献：
  名称：

  AL-MASOUDI, NAJIM A. L.;HUGHES, NEIL A., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 9, 2061-2067

  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。
• From methyl d-glucopyranoside to methyl d-allopyranoside via the Mitsunobu reaction
  作者：Mikhail Kim、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0008-6215(99)00160-3

  日期：1999.8

  Methyl β-d-glucopyranoside reacted with a 4-molar excess of the Mitsunobu reagents (triphenylphosphine–diethyl azodicarboxylate–benzoic acid) under Weinges et al. [Carbohydr. Res., 164 (1987) 453–458] conditions to furnish four differently benzoylated methyl β-d-allopyranosides in a very good overall yield. The same reaction applied to methyl α-d-glucopyranoside yielded allosides in a low yield and

  在Weinges等人的研究中，甲基β-d-吡喃葡萄糖苷与4摩尔过量的Mitsunobu试剂（三苯基膦-偶氮二羧酸二乙酯-苯甲酸）反应。[碳水化合物。Res。，164（1987）453–458]条件提供了四种不同的苯甲酰化的甲基β-d-吡喃果糖苷，总收率非常好。应用于甲基α-d-吡喃葡萄糖苷的相同反应以低收率产生了同素苷，并产生了其他九种糖产品。这些结果使我们深入了解了Mitsunobu酯化-转化反应的过程。
• The Solvolysis of Sulfonyl Esters of Methyl α-D-Glucopyranoside and Methyl α-D-Altropyranoside¹
  作者：Roger W. Jeanloz、Dorothy A. Jeanloz

  DOI：10.1021/ja01554a029

  日期：1958.11
• Al-Masoudi, Najim A. L.; Hughes, Neil A., Journal of the Chemical Society. Perkin transactions I, 1987, p. 2061 - 2068
  作者：Al-Masoudi, Najim A. L.、Hughes, Neil A.

  DOI：——

  日期：——