3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime | 88851-59-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime
• 英文别名: 3,4,6-Tri-O-acetyl-1,5-anhydro-D-fructose oxime；[(2R,3S,4R)-3,4-diacetyloxy-5-hydroxyiminooxan-2-yl]methyl acetate
• CAS: 88851-59-6
• 化学式: C₁₂H₁₇NO₈
• 分子量: 303.269
• InChiKey: GDVOYDODDMVRDW-IJLUTSLNSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  430.7±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime 在 titanium(III) chloride 、 ammonium acetate 、 sodium acetate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 6.0h， 生成 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose
  参考文献：
  名称：

  ASCOPYRONE P: CHEMICAL SYNTHESIS FROM d-GLUCOSE

  摘要：

  The pyranone, 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (1) (ascopyrone P), has been synthesised in eight steps from D-glucose. The key steps were deacetylation of 3,6-di-O-acetyl-1,5-anhydro-D-glycero-hex-3-en-2-ulose (8) to give isomers and hydrates of 1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulose (9). Isomerisation of this mixture afforded 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (1) (ascopyrone P) in a moderate yield.

  DOI：

  10.1081/car-120016855
• 作为产物：
  描述：

  [(2R,3R,4S)-4,5-二乙酰氧基-2-(乙酰氧基甲基)-3,4-二氢-2H-吡喃-3-基]乙酸酯 在 吡啶 、 盐酸羟胺 作用下， 反应 24.0h， 以61%的产率得到3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime
  参考文献：
  名称：

  ASCOPYRONE P: CHEMICAL SYNTHESIS FROM d-GLUCOSE

  摘要：

  The pyranone, 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (1) (ascopyrone P), has been synthesised in eight steps from D-glucose. The key steps were deacetylation of 3,6-di-O-acetyl-1,5-anhydro-D-glycero-hex-3-en-2-ulose (8) to give isomers and hydrates of 1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulose (9). Isomerisation of this mixture afforded 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose (1) (ascopyrone P) in a moderate yield.

  DOI：

  10.1081/car-120016855

文献信息

• Anti-oxidant
  申请人：——

  公开号：US20020051840A1

  公开（公告）日：2002-05-02

  The present invention provides an anti-oxidant composition comprising a cyclic compound having formula I or a derivative thereof, wherein R 1 and R 2 are indepednetly selected from —OH, ═O, wherein R 3 is a substituent comprising an —OH group; and wherein R 4 and R 5 are other than H; with the proviso that the compound is other than ascorbic acid.

  本发明提供一种抗氧化剂组合物，包括具有式I或其衍生物的环状化合物，其中R1和R2独立地选自—OH，═O，其中R3是含有—OH基团的取代基；且其中R4和R5不同于氢；但化合物不包括抗坏血酸。
• Lichtenthaler, Frieder W.; Jarglis, Pan; Hempe, Walter, Liebigs Annalen der Chemie, 1983, # 11, p. 1959 - 1972
  作者：Lichtenthaler, Frieder W.、Jarglis, Pan、Hempe, Walter

  DOI：——

  日期：——