3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose | 297768-00-4

• 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
• 英文别名: 3,4,6-tri-O-acetyl-1,5-anhydro-D-fructose；[(2R,3R,4S)-3,4-diacetyloxy-5-oxooxan-2-yl]methyl acetate
• CAS: 297768-00-4
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: YIZKUFIXCHQKPM-IJLUTSLNSA-N

物化性质

• 熔点：
  89-90 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  391.4±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 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：
  105
• 氢给体数：
  0
• 氢受体数：
  8

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 在 sodium acetate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以91%的产率得到3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose
  参考文献：
  名称：

  Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (−)-bissetone and (−)-palythazine

  摘要：

  High-yielding protocols are described to convert D-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and beta-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-D-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.019
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime 在 titanium(III) chloride 、 ammonium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以27%的产率得到3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-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
• 作为试剂：
  描述：

  3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime 、 、 、 氯仿 、 1,4-二氧六环 在 ice 、 氯仿 、 碳酸氢钠 、 水 、 magnesium sulfate 、 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose 、 乙醚 作用下， 反应 3.0h， 生成 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose
  参考文献：
  名称：

  Anti-oxidant

  摘要：

  本发明提供一种抗氧化剂组合物，其包括具有式I或其衍生物的环状化合物，其中R1和R2分别选择自—OH、═O，其中R3是包括—OH基团的取代基；而R4和R5则不是氢；但该化合物不包括抗坏血酸。

  公开号：

  US06846505B2

文献信息

• Structure of 1,5-Anhydro-D-fructose: X-ray Analysis of Crystalline Acetylated Dimeric Forms
  作者：Søren M. Andersen、Inge Lundt、Jan Marcussen、I. Søtofte、Shukun Yu

  DOI：10.1080/07328309808001881

  日期：1998.9.1

  Acetylation of 1,5-anhydro-D-fructose under acidic conditions gave two crystalline acetylated dimeric forms, which by X-ray analysis were shown to be diastereomeric spiroketals formed between C-2 and C-2/C-3. The structures of the compounds differed only at the configuration at C-2. Acetylation or benzoylation of 1,5-anhydro-D-fructose in pyridine yielded 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enos-2-ulopyra-nose or crystalline 1,5-anhydro-3,6-di-O-benzoyl-4-deoxy-D-glycero-hex-3-enos-2-ulo-pyranose.
• ANTI-OXIDANT
  申请人：DANISCO A/S

  公开号：EP1169409A1

  公开（公告）日：2002-01-09
• US6846505B2
  申请人：——

  公开号：US6846505B2

  公开（公告）日：2005-01-25
• [EN] ANTI-OXIDANT<br/>[FR] ANTIOXYDANT
  申请人：DANISCO

  公开号：WO2000056838A1

  公开（公告）日：2000-09-28

  There is provided an anti-oxidant composition comprising a cyclic compound having formula (I) or a derivative thereof, wherein R?1 and R2¿ are independently selected from -OH, =O, wherein R3 is a substituent comprising an -OH group; and wherein R?4 and R5¿ are other than H; with the proviso that the compound is other than ascorbic acid.