[(2R,3S,4R)-3-acetyloxy-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate | 149883-68-1

• 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: [(2R,3S,4R)-3-acetyloxy-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 149883-68-1
• 化学式: C₂₄H₃₂O₁₅
• 分子量: 560.509
• InChiKey: IJCYECCDDPPETD-RELJMNFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-3-acetyloxy-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate 在 sodium azide 、 ammonium cerium(IV) nitrate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 Acetic acid (2R,3S,4R,5R)-6-acetoxy-2-acetoxymethyl-5-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  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.

  DOI：

  10.1021/jo00068a030
• 作为产物：
  描述：

  乙酸酐 、 D-葡萄烯糖 、 4-硝基苯基-D-吡喃葡糖苷 在 吡啶 作用下， 生成 [(2R,3S,4R)-3-acetyloxy-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate 、 [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-yl]methoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  galβ1,3glucal的简便酶促合成：Le a和唾液酸Le a合成的关键中间体

  摘要：

  已经研究了几种糖苷酶在各种供体糖和糖受体之间糖苷键形成中的区域选择性。关键关注的是β-半乳糖苷酶介导的半乳糖与葡萄糖的偶联，从而提供具有高区域选择性的β-1,3-联二糖。

  DOI：

  10.1016/s0040-4039(00)74231-6