2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-β-D-mannopyranosylamine | 850813-88-6

• 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: 2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-β-D-mannopyranosylamine
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(2-chloroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 850813-88-6
• 化学式: C₁₆H₂₂ClNO₁₀
• 分子量: 423.804
• InChiKey: FBGCOAPWUMWSSA-NZBFACKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-β-D-mannopyranosylamine 在 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 生成 (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-iodoacetamido)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  基于使用N-（β-糖基）碘乙酰胺的硝基乙酸乙酯的烷基化合成N-（β-糖基）天冬酰胺的新策略

  摘要：

  已经开发了一种概念上新颖的策略，用于通过使用六种衍生自单糖和二糖的过氧乙酰化N-（β-糖基）碘乙酰胺对硝基乙酸乙酯进行烷基化，以高收率合成N-（β-糖基）天冬酰胺前体。。使用手性有机催化剂，N-（9-蒽基甲基）辛基氯化铵（10mol％），导致高达64％de的非对映选择性烷基化。对Glc衍生物的纯化的主要非对映异构体的单晶结构分析显示，在作为L-天冬酰胺缀合物的前体的单取代的硝基乙酸乙酯的α-碳上，S的绝对构型。

  DOI：

  10.1016/j.tetlet.2010.08.072
• 作为产物：
  描述：

  1-氨基-1-脱氧-beta-D-吡喃甘露糖 在 Na β-zeolite 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-β-D-mannopyranosylamine
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402

文献信息

• Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators
  作者：Manoharan Mathiselvam、Duraikkannu Loganathan、Babu Varghese

  DOI：10.1039/c3ra42041h

  日期：——

  hydrogelating ability as compared to thiourea linked glycolipids. The influence of sugar head group and alkyl chain length on the glycolipid’s self-assembly has also been studied. The fibrillar structures of the supramolecular hydrogels have been characterized by scanning electron microscopy (SEM). The thermal properties of the hydrogels formed by urea linked glycolipids have been studied by differential scanning

  通过使糖基氨基乙酰胺与烷基异硫氰酸酯和异氰酸酯反应，已经合成了具有硫脲和脲连接基的新型糖脂作为低分子量胶凝剂。研究了连接基团对其自组装性能的影响。对获得的新糖脂在各种溶剂中的胶凝研究表明，它们是良好的水凝剂。与硫脲连接的糖脂相比，尿素连接的糖脂显示出更好的水凝胶化能力。还研究了糖首基和烷基链长对糖脂自组装的影响。超分子水凝胶的原纤维结构已经通过扫描电子显微镜（SEM）表征。由尿素连接的糖脂形成的水凝胶的热性质已通过差示扫描量热法（DSC）和VT-NMR进行了研究。已经通过小角度（SAXS）和单晶X射线衍射方法研究了分子堆积。
• SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides
  作者：Laxminarayan Sahoo、Anadi Singhamahapatra、Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2013.07.110

  日期：2013.9

  A method for the chemoselective reduction of glycopyranosyl azides using SnCl4 and tin metal as the reducing agent followed by in situ chloroacetylation of the synthesized glycopyranosyl amine was developed. This reaction is applicable to diversely functionalized glycopyranosyl azides for the synthesis of glycopyranosyl chloroacetamides. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of ClusterN-Glycosides Based on aβ-Cyclodextrin Core
  作者：Juan J. García-López、Francisco Santoyo-González、Antonio Vargas-Berenguel、Juan J. Giménez-Martínez

  DOI：10.1002/(sici)1521-3765(19990604)5:6<1775::aid-chem1775>3.0.co;2-2

  日期：1999.6.4

  A convenient method for the synthesis of beta-D-gluco-, beta-D-galacto-, 2-acetamido-2-deoxy-beta-D-gluco- and alpha-D-mannopyranosylamine clusters based on cyclomaltoheptaose (beta-cyclodextrin) is presented. The synthesis involves: 1) the one-pot synthesis of the acetylated chloroacetyl N-glycoside derivatives of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-glucose and D-mannose from the corresponding glycosyl azides, 2) conversion of the chloroacetyl N-glycosides into their isothiouronium derivatives, then 3) attachment of the N-glycosides onto heptakis(6-deoxy-6-iodo) and heptakis(6-chloroacetamido-6-deoxy) beta-cyclodextrin by means of nucleophilic displacement with caesiurn carbonate in dimethylformamide, and 4) de-O-acetylation of beta-cyclodextrin derivatives. The chloroacetyl N-glycoside derivatives were easily prepared by mild reduction of the azide function by one of two methods: a) by the Staudinger reaction, with nBu(3)P, and b) with 1,3-propanedithiol, as reducing reagents.