2,3-O-isopropylidene-4-chloro-4-deoxy-hex-5-ulose dimethyl acetal | 928854-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-4-chloro-4-deoxy-hex-5-ulose dimethyl acetal
• 英文别名: (1R)-1-chloro-1-[(4R,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropan-2-one
• CAS: 928854-29-9
• 化学式: C₁₁H₁₉ClO₆
• 分子量: 282.721
• InChiKey: KQPFXQKETIXYQB-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-4-chloro-4-deoxy-hex-5-ulose dimethyl acetal 、 4-硝基邻苯二胺 生成 2-((5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-7-nitroquinoxaline
  参考文献：
  名称：

  An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities

  摘要：

  A novel and efficient method for the synthesis of quinoxaline derivatives has been developed. Isopropylidenation of 4-chloro-4-deoxy-alpha-D-galactose with 2,2-dimethoxypropane, followed by selective hydrolysis, afforded 2,3-O-isopropylidene-4-chloro-4-deoxy-D-galactose di-methyl acetal (3) as a sole product. Oxidation of compound 3 with (Bu3Sn)(2)O-Br-2 gave corresponding hex-5-ulose derivative in high yields. The hex-5-ulose derivative reacted with o-phenylenediamines under neutral conditions to afford quinoxaline derivatives in reasonable yields. The in vitro cytotoxic activities of these quinoxaline derivatives were investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.007
• 作为产物：
  描述：

  4-chloro-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose dimethyl acetal 在 溴 、 溶剂黄146 、 三丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 53.0h， 生成 2,3-O-isopropylidene-4-chloro-4-deoxy-hex-5-ulose dimethyl acetal
  参考文献：
  名称：

  An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities

  摘要：

  A novel and efficient method for the synthesis of quinoxaline derivatives has been developed. Isopropylidenation of 4-chloro-4-deoxy-alpha-D-galactose with 2,2-dimethoxypropane, followed by selective hydrolysis, afforded 2,3-O-isopropylidene-4-chloro-4-deoxy-D-galactose di-methyl acetal (3) as a sole product. Oxidation of compound 3 with (Bu3Sn)(2)O-Br-2 gave corresponding hex-5-ulose derivative in high yields. The hex-5-ulose derivative reacted with o-phenylenediamines under neutral conditions to afford quinoxaline derivatives in reasonable yields. The in vitro cytotoxic activities of these quinoxaline derivatives were investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.007

文献信息

• An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities
  作者：Lin Yan、Feng-Wu Liu、Gui-Fu Dai、Hong-Min Liu

  DOI：10.1016/j.bmcl.2006.11.007

  日期：2007.2

  A novel and efficient method for the synthesis of quinoxaline derivatives has been developed. Isopropylidenation of 4-chloro-4-deoxy-alpha-D-galactose with 2,2-dimethoxypropane, followed by selective hydrolysis, afforded 2,3-O-isopropylidene-4-chloro-4-deoxy-D-galactose di-methyl acetal (3) as a sole product. Oxidation of compound 3 with (Bu3Sn)(2)O-Br-2 gave corresponding hex-5-ulose derivative in high yields. The hex-5-ulose derivative reacted with o-phenylenediamines under neutral conditions to afford quinoxaline derivatives in reasonable yields. The in vitro cytotoxic activities of these quinoxaline derivatives were investigated. (c) 2006 Elsevier Ltd. All rights reserved.