methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose | 838838-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose
• 英文别名: 2-[(2R,4aR,6S,8S,8aS)-6-methoxy-7-oxo-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl]acetaldehyde
• CAS: 838838-31-6
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: HYUHIVVNXCTMNG-DEDQRHPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose 在 羟胺 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (3aR,4S,5R,7S,7aS)-5-Hydroxymethyl-7-methoxy-hexahydro-pyrano[3,4-b]pyrrole-1,4-diol
  参考文献：
  名称：

  Ring-closing double reductive amination route to aza-heteroannulated sugars

  摘要：

  1.4-Dicarbonyl derivatives of glycosides are produced by ozonolysis or Wacker oxidation. A stable ozonide is isolated and a carbonyl group reduced whilst maintaining the ozonide functionality. The 1,4-dicarbonyl compounds are converted to various N-substituted pyrrolidines by diastereoselective double reductive amination The resulting aza-heteroannulated sugars no significant inhibition of any glycosidase, with the exception of compound 12g. which is a weak inhibitor Of beta-galactosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.032
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose 在 polymer-bound PPh₃ 、 臭氧 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose
  参考文献：
  名称：

  Ring-closing double reductive amination route to aza-heteroannulated sugars

  摘要：

  1.4-Dicarbonyl derivatives of glycosides are produced by ozonolysis or Wacker oxidation. A stable ozonide is isolated and a carbonyl group reduced whilst maintaining the ozonide functionality. The 1,4-dicarbonyl compounds are converted to various N-substituted pyrrolidines by diastereoselective double reductive amination The resulting aza-heteroannulated sugars no significant inhibition of any glycosidase, with the exception of compound 12g. which is a weak inhibitor Of beta-galactosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.032

文献信息

• Stereoselective synthesis by double reductive amination ring closure of novel aza-heteroannulated sugars
  作者：Dominic M. Laventine、Michelle Davies、Emma L. Evinson、Paul R. Jenkins、Paul M. Cullis、Marcos D. García

  DOI：10.1016/j.tet.2009.04.011

  日期：2009.6

  We present here the stereoselective synthesis of a series of 2/3-N-pyrrolidine derivatives of glycosides produced by diastereoselective double reductive amination ring closure of 1,4-dicarbonyl compounds. These precursors were produced by tandem ozonolysis–reduction or Wacker oxidation of known alkenes. The potential of these new compounds as glycosidase inhibitors is illustrated for compound 16, showing

  我们在这里介绍了由1，4-二羰基化合物的非对映选择性双还原胺化闭环产生的一系列2 / 3- N-吡咯烷糖苷衍生物的立体选择性合成。这些前体是通过串联臭氧分解-还原或瓦克氧化已知烯烃而制得的。这些新化合物作为糖苷酶抑制剂的潜力在化合物16中得到了说明，显示出对β- d-半乳糖苷酶的选择性抑制。
• Ring-closing double reductive amination route to aza-heteroannulated sugars
  作者：Dominic M. Laventine、Michelle Davies、Emma L. Evinson、Paul R. Jenkins、Paul M. Cullis、John Fawcett

  DOI：10.1016/j.tetlet.2004.11.032

  日期：2005.1

  1.4-Dicarbonyl derivatives of glycosides are produced by ozonolysis or Wacker oxidation. A stable ozonide is isolated and a carbonyl group reduced whilst maintaining the ozonide functionality. The 1,4-dicarbonyl compounds are converted to various N-substituted pyrrolidines by diastereoselective double reductive amination The resulting aza-heteroannulated sugars no significant inhibition of any glycosidase, with the exception of compound 12g. which is a weak inhibitor Of beta-galactosidase. (C) 2004 Elsevier Ltd. All rights reserved.