N-benzyl-D-gluconamide | 100569-46-8

• 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-benzyl-D-gluconamide
• 英文别名: N-benzyl gluconamide；D-gluconic acid benzylamide；D-Gluconsaeure-benzylamid；N-Benzyl-D-gluconsaeureamid；(2R,3S,4R,5R)-N-benzyl-2,3,4,5,6-pentahydroxyhexanamide
• CAS: 100569-46-8；5438-33-5
• 化学式: C₁₃H₁₉NO₆
• 分子量: 285.297
• InChiKey: DMWRWTMLTXLUSX-WISYIIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  N-benzyl-D-gluconamide 、 乙酸酐 在 吡啶 作用下， 反应 8.0h， 以421 mg的产率得到N-benzyl 2,3,4,5,6-O-pentaacetyl-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
• 作为产物：
  描述：

  苄胺 、 (3R,4R,5R)-5-[(1R)-1,2-二羟基乙基]-3,4-二羟基四氢呋喃-2-酮 以 水 为溶剂， 生成 N-benzyl-D-gluconamide
  参考文献：
  名称：

  Kuhn,R.; Jochims,J.C., Chemische Berichte, 1960, vol. 93, p. 1047 - 1052

  摘要：

  DOI：

文献信息

• van Wijk, Recueil des Travaux Chimiques des Pays-Bas, 1921, vol. 40, p. 232
  作者：van Wijk

  DOI：——

  日期：——
• Synthesis of crosslinked nanostructured saccharidic vinyl copolymers and their functionalization
  作者：Vincenzo Bertini、Marco Pocci、Silvana Alfei、Barbara Idini、Francesco Lucchesini

  DOI：10.1016/j.tet.2007.08.106

  日期：2007.11

  Saccharidic monomers and a macromonomer were synthesized and copolymerized in the presence of divinylbenzene (DVB) as crosslinker in conditions of separation of phases to give hydrophilic nanostructured sugar-based vinyl copolymers. Appropriate model molecules such as N-benzyl-D-gluconamide for the saccharidic copolymers and 4-(4-chlorobutoxy) benzaldehyde and (E)-4-(4-chloro-2-butenyloxy) benzaldehyde for electrophilic reagents prefiguring possible copper amine oxidase inhibitors allowed identification of conditions for useful monofunctionalizations mainly at the position 2 of the saccharidic units. The examined samples of the nanostructured copolymers from one of the monomers proved to be stable enough to tolerate the functionalization reactions without loss of morphology. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of d-gluconamides as green mineral scales
  作者：Marcelo I.P. Reis、Aline D. Gonçalves、Fernando de C. da Silva、Alessandro K. Jordão、Ricardo J. Alves、Saulo Fernandes de Andrade、Jackson A.L.C. Resende、Anderson A. Rocha、Vitor F. Ferreira

  DOI：10.1016/j.carres.2012.01.027

  日期：2012.5

  A series of 13 D-gluconamides were synthesized in moderate to good yields and evaluated as green scale inhibitors. The crystal structures of two compounds were determined by X-ray crystallography. The compounds 6c and 6d showed a reasonable inhibition of BaSO4 precipitation from aqueous solution (47% and 51%, respectively) that indicated the potential for these derivatives of delta-gluconolactone. (C) 2012 Elsevier Ltd. All rights reserved.
• Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Unprotected Carbohydrate Molecules
  作者：Chia-Ching Cho、Jia-Nan Liu、Chung-Hsun Chien、Jiun-Jie Shie、Ying-Chu Chen、Jim-Min Fang

  DOI：10.1021/jo802338k

  日期：2009.2.20

  With use of iodine as an appropriate oxidant, unprotected and unmodified aldoses undergo oxidative amidation with a variety of functionalized amines, α-amino esters, and peptides, whereas KDO, sialic acid, and other α-keto acids proceed with oxidative decarboxylation followed by in situ amidation. Glycoside bond and many other functional groups are inert under such mild reaction conditions. This reaction

  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。
• Kuhn,R.; Jochims,J.C., Chemische Berichte, 1960, vol. 93, p. 1047 - 1052
  作者：Kuhn,R.、Jochims,J.C.

  DOI：——

  日期：——