2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-α-D-mannopyranosylamine | 229024-59-3

• 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-α-D-mannopyranosylamine
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[(2-chloroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 229024-59-3
• 化学式: C₁₆H₂₂ClNO₁₀
• 分子量: 423.804
• InChiKey: FBGCOAPWUMWSSA-VMMWWAARSA-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：

  硫脲 、 2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-α-D-mannopyranosylamine 以 丙酮 为溶剂， 反应 72.0h， 以80%的产率得到2,3,4,6-Tetra-O-acetyl-N-(isothiouronium acetyl)-α-D-mannopyranosylamine hydrochloride
  参考文献：
  名称：

  Synthesis of ClusterN-Glycosides Based on aβ-Cyclodextrin Core

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1775::aid-chem1775>3.0.co;2-2
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-叠氮化吡喃甘露糖 以 二氯甲烷 为溶剂， 生成 2,3,4,6-Tetra-O-acetyl-N-chloroacetyl-α-D-mannopyranosylamine
  参考文献：
  名称：

  Synthesis of ClusterN-Glycosides Based on aβ-Cyclodextrin Core

  摘要：

  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.

  DOI：

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

文献信息

• 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.