2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose | 68733-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose
• 英文别名: [(2S)-5-acetyloxy-4-oxo-2,3-dihydropyran-2-yl]methyl acetate
• CAS: 68733-00-6
• 化学式: C₁₀H₁₂O₆
• 分子量: 228.202
• InChiKey: ZAHGOTQUKKNVHC-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以68%的产率得到2-呋喃基羟基甲基甲酮
  参考文献：
  名称：

  A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose

  摘要：

  The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydroD-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.037
• 作为产物：
  描述：

  1,5-脱水-d-果糖 在 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose
  参考文献：
  名称：

  A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose

  摘要：

  The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydroD-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.037

文献信息

• A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose
  作者：Mikkel Andreassen、Inge Lundt

  DOI：10.1016/j.carres.2006.03.037

  日期：2006.7

  The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydroD-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1). (c) 2006 Elsevier Ltd. All rights reserved.