N-ethyl-D-gluconamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-ethyl-D-gluconamide
• 英文别名: N-ethyl gluconamide；(2R,3S,4R,5R)-N-ethyl-2,3,4,5,6-pentahydroxyhexanamide
• 化学式: C₈H₁₇NO₆
• 分子量: 223.226
• InChiKey: CEUIEPMYCRNXIZ-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N-ethyl-D-gluconamide 在 吡啶 作用下， 反应 24.0h， 以85%的产率得到2,3,4,5,6-penta-O-acetyl-N-ethyl-D-gluconamide
  参考文献：
  名称：

  Optically active sugar thioamides from δ-gluconolactone

  摘要：

  This paper describes a facile and rapid approach to N-alkyl- and N-aryl-thiogluconamides employing delta-gluconolactone as starting material. The protocol involves a three-step sequence to afford the corresponding thioamides as crystalline substances in moderate to good yields. The Lawesson reagent was found to be the reagent of choice to accomplish the key transformation amide-thioamide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00140-3
• 作为产物：
  描述：

  葡萄糖 、 乙胺盐酸盐 在 碘 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以100%的产率得到N-ethyl-D-gluconamide
  参考文献：
  名称：

  醛糖的直接酰胺化和α-酮酸的脱羧酰胺化：一种未保护的碳水化合物分子的有效共轭方法

  摘要：

  通过使用碘作为适当的氧化剂，未保护和未修饰的醛糖会与各种功能化的胺，α-氨基酯和肽进行氧化酰胺化，而KDO，唾液酸和其他α-酮酸会继续进行氧化脱羧反应原位酰胺化。在这种温和的反应条件下，糖苷键和许多其他官能团是惰性的。用于糖分子的直接连接的该反应方案在糖缀合物的一般和有效合成的发展中看起来是有希望的。

  DOI：

  10.1021/jo802338k

文献信息

• Small molecule ice recrystallization inhibitors and methods of use thereof
  申请人：THE UNIVERSITY OF OTTAWA

  公开号：US10004222B2

  公开（公告）日：2018-06-26

  Ice recrystallization inhibitor (IRI) compounds and methods for cryopreserving umbilical cord blood are provided. The compounds are unsubstituted, mono-substituted, or di-substituted aryl-aldonamides. The methods include fractionating whole umbilical cord blood to generate a fraction comprising hematopoietic stem cells, mixing the hematopoietic stem cells with at least one IRI compound to form an IRI suspension, and freezing the IRI suspension.

  本研究提供了用于冷冻保存脐带血的冰再结晶抑制剂（IRI）化合物和方法。这些化合物是未取代的、单取代的或双取代的芳基-醛酰胺类化合物。这些方法包括分馏整个脐带血以产生包含造血干细胞的部分，将造血干细胞与至少一种IRI化合物混合以形成IRI悬浮液，并冷冻IRI悬浮液。
• SMALL MOLECULE ICE RECRYSTALLIZATION INHIBITORS AND METHODS OF USE THEREOF
  申请人：THE UNIVERSITY OF OTTAWA

  公开号：US20150157010A1

  公开（公告）日：2015-06-11

  The invention relates to small molecule ice recrystallization inhibitor (IRI) compounds having increased ice recrystallization inhibition activity. The IRI compounds disclosed herein are useful in compositions, kits and methods for cryopreserving biological material such as organs, tissues and cells.
• Small Molecule Ice Recrystallization Inhibitors And Methods Of Use Thereof
  申请人：THE UNIVERSITY OF OTTAWA

  公开号：US20150373968A1

  公开（公告）日：2015-12-31

  Ice recrystallization inhibitor (IRI) compounds and methods for cryopreserving umbilical cord blood are provided. The compounds are unsubstituted, mono-substituted, or di-substituted aryl-adlonamides. The methods include fractionating whole umbilical cord blood to generate a fraction comprising hematopoietic stem cells, mixing the hematopoietic stem cells with at least one IRI compound to form an IRI suspension, and freezing the IRI suspension.
• US9648869B2
  申请人：——

  公开号：US9648869B2

  公开（公告）日：2017-05-16
• [EN] SMALL MOLECULE ICE RECRYSTALLIZATION INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE RECRISTALLISATION DE GLACE À PETITES MOLÉCULES ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：UNIV OTTAWA

  公开号：WO2013175299A1

  公开（公告）日：2013-11-28

  The invention relates to small molecule ice recrystallization inhibitor (IRI) compounds having increased ice recrystallization inhibition activity. The IRI compounds disclosed herein are useful in compositions, kits and methods for cryopreserving biological material such as organs, tissues and cells.