3,4,6-tri-O-acetyl-1,5-anhydro-D-fructose E-oxime | 75414-20-9

• 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-fructose E-oxime
• 英文别名: [(2R,3S,4R,5E)-3,4-diacetyloxy-5-hydroxyiminooxan-2-yl]methyl acetate
• CAS: 75414-20-9
• 化学式: C₁₂H₁₇NO₈
• 分子量: 303.269
• InChiKey: GDVOYDODDMVRDW-OGQBYSKKSA-N

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-fructose E-oxime 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 吡啶 、 四氯化碳 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Lichtenthaler, Frieder W.; Jarglis, Pan, Angewandte Chemie, 1982, vol. 94, # 8, p. 643 - 644

  摘要：

  DOI：
• 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 16.0h， 生成 3,4,6-tri-O-acetyl-1,5-anhydro-D-fructose E-oxime
  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

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。
• Selective deacylation of enol esters with hydroxylamine
  作者：Frieder W. Lichtenthaler、Pan Jarglis

  DOI：10.1016/s0040-4039(00)92736-9

  日期：——
• US6846505B2
  申请人：——

  公开号：US6846505B2

  公开（公告）日：2005-01-25