D-glucarate-6,3-lactone ethyl ester | 261900-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: D-glucarate-6,3-lactone ethyl ester
• 英文别名: ethyl D-glucarate 6,3-lactone；ethyl glucarate-6,3-lactone；D-glucaric acid-1-ethyl ester-6=>3-lactone；D-Glucarsaeure-1-aethylester-6=>3-lacton；ethyl (2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetate
• CAS: 261900-70-3
• 化学式: C₈H₁₂O₇
• 分子量: 220.179
• InChiKey: ZHYNMZABMJWURC-MOJAZDJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  D-glucarate-6,3-lactone ethyl ester 生成 D-glucaro-1,4:6,3-dilactone
  参考文献：
  名称：

  Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions

  摘要：

  Convenient procedures are described for the preparation of hydroxylated nylons (polyhydroxypolyamides) from D-glucaric acid. The procedures, which do not require protection/deprotection of carbohydrate hydroxyl groups, can be used to make a variety of polymers with a range of properties from D-glucaric acid. Simple alcohol (e.g. methanol or ethanol) esterification mixtures of D-glucaric acid (from oxidation of D-glucose) were reacted with bis-primary diamines in a polar solvent, typically methanol, to produce the polyamides. D-Glucaric acid esterification mixtures contain varying amounts of dialkyl D-glucarate, alkyl D-glucarate 1,4-lactone, and alkyl D-glucarate 6,3-lactone. These ester forms of D-glucaric acid are also in equilibrium under the conditions of the polymerization. Diamines employed included linear alkylenediamines, a branched alkylenediamine, arylalkylenediamines, and diamines with oxygen or nitrogen atoms in the alkylene chain. Considerable differences in polymer physical properties were observed by changing the diamine monomer. Linear aliphatic and arylalkylenediamines gave crystalline solid polyamides with high melting points. The C2 and C4 diamine copolymers were water soluble, whereas the C6 and above were water insoluble. The branched diamine copolymer and those with oxygen or nitrogen in the diamine chain had lower melting points and higher alcohol solubility than the unbranched alkylenediamine copolymers.

  DOI：

  10.1021/ja00081a018
• 作为产物：
  描述：

  diethyl glucarate 在 palladium 10% on activated carbon 、 氢气 、 甲基三氧化铼(VII) 作用下， 以 乙醇 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 D-glucarate-6,3-lactone ethyl ester
  参考文献：
  名称：

  [EN] DEOXYDEHYDRATION OF SUGAR DERIVATIVES
  [FR] DÉSOXYDÉSHYDRATATION DE DÉRIVÉS DE SUCRE

  摘要：

  公开号：

  WO2017147098A8

文献信息

• Hydrogen Gas-Mediated Deoxydehydration/Hydrogenation of Sugar Acids: Catalytic Conversion of Glucarates to Adipates
  作者：Reed T. Larson、Andrew Samant、Jianbin Chen、Woojin Lee、Martin A. Bohn、Dominik M. Ohlmann、Stephan J. Zuend、F. Dean Toste

  DOI：10.1021/jacs.7b07801

  日期：2017.10.11

  of polyhydroxylated biomass into industrially relevant feedstock chemicals is described. This system includes a bimetallic Pd/Re catalyst in combination with hydrogen gas as a terminal reductant and enables the high-yielding reduction of sugar acids. This procedure has been applied to the synthesis of adipate esters, precursors for the production of Nylon-6,6, in excellent yield from biomass-derived

  描述了用于将多羟基化生物质转化为工业相关原料化学品的操作简单、可扩展的系统的开发。该系统包括双金属 Pd/Re 催化剂和作为末端还原剂的氢气，能够实现糖酸的高产还原。该程序已应用于合成己二酸酯，即生产尼龙 6,6 的前体，从生物质来源中以优异的产量合成。
• DEOXYDEHYDRATION OF SUGAR DERIVATIVES
  申请人：The Regents of The University of California Santa Cruz

  公开号：EP3333152A1

  公开（公告）日：2018-06-13

  The disclosure provides methods for deoxydehydration of sugar-based derivatives using hydrogen gas as a reducing agent.

  本公开提供了使用氢气作为还原剂进行糖基衍生物脱氧脱水的方法。
• Zinner; Fischer, Chemische Berichte, 1956, vol. 89, p. 1503,1506
  作者：Zinner、Fischer

  DOI：——

  日期：——
• US5312967A
  申请人：——

  公开号：US5312967A

  公开（公告）日：1994-05-17
• [EN] DEOXYDEHYDRATION OF SUGAR DERIVATIVES<br/>[FR] DÉSOXYDÉSHYDRATATION DE DÉRIVÉS DE SUCRE
  申请人：UNIV CALIFORNIA

  公开号：WO2017147098A8

  公开（公告）日：2017-11-16