3-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester | 193748-50-4

• 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: 3-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS: 193748-50-4
• 化学式: C₂₁H₂₇NO₁₃S
• 分子量: 533.51
• InChiKey: XKIBDMBQWCJMED-DJSIVUHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  178.11
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N,N,N,N-四(3-氨基丙基)-1,4-丁二胺 、 3-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到
  参考文献：
  名称：

  Synthesis of Glycodendrimers by Modification of Poly(propylene imine) Dendrimers

  摘要：

  AbstractThe use of preformed poly‐(propylene imine) dendrimers (DAB‐dendr‐(NH2)x) for the rapid and facile construction of high molecular weight carbohydrate‐coated dendrimers (glyco‐dendrimers) is presented. An efficient attachment of spacer‐armed derivatives of D‐galactose and lactose to the primary amino end groups of DAB‐dendr‐(NH2)x has been achieved by means of amide bond formation, using the N‐hydroxysuccinimide coupling procedure. Acetate protecting groups have been employed in order to avoid side reactions at the coupling stage. Deacetylation leads to the target glycodendrimers. The reactivity of all the available DAB‐dendr‐(NH2)x (generations 1–5) has been investigated and a series of homologous carbohydrate‐coated dendrimers have been synthesized. In addition, the attachment of larger saccharide moieties has been demonstrated by the condensation of a trisgalactoside cluster with DAB‐dendr‐(NH2)x carrying both four and eight primary amino groups. The regularity of the glycodendrimers has been proven by NMR spectroscopy, and the molecular weights of the low‐generation carbohydrate‐coated dendrimers have been determined by mass spectrometry. Modifications of DAB‐dendr‐(NH2)x with biologically active carbohydrates affords a new and simple approach to high molecular weight compounds that may be considered as neoglycoconjugates with perfectly symmetrical structures and that offer much promise as multivalent ligands involved in carbohydrate‐protein interactions.

  DOI：

  10.1002/chem.19970030620
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 2,3,4,6-tetra-O-acetyl-1-S-mercaptopropionyl-β-D-galactose 在 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.0h， 以93%的产率得到3-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Synthesis of Glycodendrimers by Modification of Poly(propylene imine) Dendrimers

  摘要：

  AbstractThe use of preformed poly‐(propylene imine) dendrimers (DAB‐dendr‐(NH2)x) for the rapid and facile construction of high molecular weight carbohydrate‐coated dendrimers (glyco‐dendrimers) is presented. An efficient attachment of spacer‐armed derivatives of D‐galactose and lactose to the primary amino end groups of DAB‐dendr‐(NH2)x has been achieved by means of amide bond formation, using the N‐hydroxysuccinimide coupling procedure. Acetate protecting groups have been employed in order to avoid side reactions at the coupling stage. Deacetylation leads to the target glycodendrimers. The reactivity of all the available DAB‐dendr‐(NH2)x (generations 1–5) has been investigated and a series of homologous carbohydrate‐coated dendrimers have been synthesized. In addition, the attachment of larger saccharide moieties has been demonstrated by the condensation of a trisgalactoside cluster with DAB‐dendr‐(NH2)x carrying both four and eight primary amino groups. The regularity of the glycodendrimers has been proven by NMR spectroscopy, and the molecular weights of the low‐generation carbohydrate‐coated dendrimers have been determined by mass spectrometry. Modifications of DAB‐dendr‐(NH2)x with biologically active carbohydrates affords a new and simple approach to high molecular weight compounds that may be considered as neoglycoconjugates with perfectly symmetrical structures and that offer much promise as multivalent ligands involved in carbohydrate‐protein interactions.

  DOI：

  10.1002/chem.19970030620