| 667456-67-9

• 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
• CAS: 667456-67-9
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: TWXSHEHSOFOXBJ-UOMZYOQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  260.55
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  在 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-galactopyranose
  参考文献：
  名称：

  Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

  摘要：

  The first synthesis of the tumor-associated alpha-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.126
• 作为产物：
  描述：

  methyl 2-azido-2-deoxy-D-galactopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

  摘要：

  The first synthesis of the tumor-associated alpha-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.126

文献信息

• Blocksynthese von O-glycopeptiden und anderen T-antigen strukturen
  作者：Hans Paulsen、Michael Paal

  DOI：10.1016/0008-6215(84)85006-5

  日期：1984.12

  Abstract Under the conditions of in situ anomerisation, the 2-azido-4,6-di- O -benzoyl-2-deoxy-3- O -(2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl)-α- d -galactopyranosyl bromide reacted directly and with high selectivity with the reactive hydroxyl groups of l -serine and l -threonine derivatives to form α-glycosidically-linked products. Thus, the glycopeptides containing l -serine and l -threonine

  摘要在原位异构化条件下，2-叠氮基-4,6-二-O-苯甲酰基-2-脱氧-3-O-（2,3,4,6-四-O-乙酰基-β-d -（半乳糖吡喃糖基）-α-d-半乳糖吡喃糖基溴与1-丝氨酸和1-苏氨酸衍生物的反应性羟基高选择性地直接反应，形成α-糖苷连接的产物。因此，更容易获得包含1-丝氨酸和1-苏氨酸的糖肽。二糖嵌段也可以与其他反应性羟基化合物偶联，以得到包含T受体的化合物。
• A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units
  作者：Gary C. Look、Yoshitaka Ichikawa、Gwo Jenn Shen、Pi Wan Cheng、Chi Huey Wong

  DOI：10.1021/jo00068a030

  日期：1993.7

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.