1-deoxy-2-O-ethyl-4,5-O-isopropylidene-D-erythro-hex-1-en-3-ulose | 320751-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-2-O-ethyl-4,5-O-isopropylidene-D-erythro-hex-1-en-3-ulose
• 英文别名: 2-ethoxy-1-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one
• CAS: 320751-31-3
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: BURWENCTSLUYEO-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-deoxy-2-O-ethyl-4,5-O-isopropylidene-D-erythro-hex-1-en-3-ulose 在 盐酸 、 3 A molecular sieve 、 Dowex 50 WX₈ (H⁺ form) 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.5h， 生成 (1S,2R)-1-(3-methyl-2-quinoxalinyl)-1,2,3-propanetriol
  参考文献：
  名称：

  Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

  摘要：

  1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved I-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00219-6
• 作为产物：
  描述：

  D-erythronolactone acetonide 、 乙烯基乙醚 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 以50%的产率得到1-deoxy-2-O-ethyl-4,5-O-isopropylidene-D-erythro-hex-1-en-3-ulose
  参考文献：
  名称：

  Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

  摘要：

  1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved I-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00219-6

文献信息

• Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate
  作者：Marcus A. Glomb、Christoph Pfahler

  DOI：10.1016/s0008-6215(00)00219-6

  日期：2000.11

  1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved I-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 Elsevier Science Ltd. All rights reserved.