O-(2,3,4-Tri-O-acetyl-6-desoxy-α-D-mannopyranosyl)-trichloracetimidat | 146683-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-Tri-O-acetyl-6-desoxy-α-D-mannopyranosyl)-trichloracetimidat
• CAS: 146683-30-9
• 化学式: C₁₄H₁₈Cl₃NO₈
• 分子量: 434.658
• InChiKey: CBEDSVQSHODOKN-FSVXGXJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  121.21
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-Tri-O-acetyl-6-desoxy-α-D-mannopyranosyl)-trichloracetimidat 在 palladium on activated charcoal 吡啶 、 3 A molecular sieve 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成
  参考文献：
  名称：

  Paulsen, Hans; Meinjohanns, Ernst; Reck, Folkert, Liebigs Annalen der Chemie, 1993, # 7, p. 721 - 736

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯乙腈 、 1,2,3,4-tetra-O-acetyl-D-rhamnose 在 哌啶 、 potassium carbonate 作用下， 生成 O-(2,3,4-Tri-O-acetyl-6-desoxy-α-D-mannopyranosyl)-trichloracetimidat
  参考文献：
  名称：

  Paulsen, Hans; Meinjohanns, Ernst; Reck, Folkert, Liebigs Annalen der Chemie, 1993, # 7, p. 721 - 736

  摘要：

  DOI：

文献信息

• Tris(pentafluorophenyl)borane-Catalyzed Stereoselective <i>C</i>-Glycosylation of Indoles with Glycosyl Trichloroacetimidates: Access to 3-Indolyl-<i>C</i>-glycosides
  作者：Atul Dubey、Ashwani Tiwari、Pintu Kumar Mandal

  DOI：10.1021/acs.joc.1c00698

  日期：2021.6.18

  An efficient and highly regioselective method for the synthesis of 3-indolyl-C-glycosides has been developed through coupling of glycosyl trichloroacetimidates with a wide range of substituted indoles in the presence of catalytic amounts of B(C6F5)3 within a few minutes. This methodology has a wide scope of substrates under mild reaction conditions and provides exclusively β-stereoselective 3-indolyl-C-glycosides

  为3-吲哚基的合成的高效和高度选择性方法Ç -glycosides已通过与各种取代的吲哚的在催化量的B（C存在下糖基trichloroacetimidates的耦合开发6 ˚F 5）3内几分钟。这种方法具有温和反应条件下底物的宽范围和排他地提供β立体选择性的3-吲哚基Ç在64-87％的收率-glycosides。
• Synthesis of modified oligosaccharides of N-Glycoproteins intended for substrate specificity studies of N-Acetylglucosaminyltransferases II-V
  作者：Hans Paulsen、Ernst Meinjohanns

  DOI：10.1016/s0040-4039(00)60178-8

  日期：1992.11

  Effective synthesis of the tetrasaccharide 1, substrate for GlcNAc-T II, the pentasaccharide 9, substrate for GlcNAc-T III-V, and the modified analogues 2–8 and 10–14 are developed by linking the corresponding building blocks using the trichloroacetimidate method. The specific modified substrate analogues 2–8 and 10–14 can be applied to studies of the substrate specificity of GlcNAc-T II and GlcNAc

  通过使用三氯乙酰亚氨酸酯方法连接相应的结构单元，开发了有效合成四糖1，GlcNAc-T II的底物，五糖9，GlcNAc-T III-V的底物以及修饰的类似物2-8和10-14的方法。 。特定的修饰底物类似物2-8和10-14可分别用于研究GlcNAc-T II和GlcNAc T III-V的底物特异性。修饰的四糖8和五糖14也可以分别用作GlcNAc-T IV和GlcNAc-T V的潜在特异性底物。
• Paulsen, Hans; Springer, Matthias; Reck, Folkert, Liebigs Annalen, 1995, # 1, p. 53 - 66
  作者：Paulsen, Hans、Springer, Matthias、Reck, Folkert、Meinjohanns, Ernst、Brockhausen, Inka、Schachter, Harry

  DOI：——

  日期：——
• Synthesis of a Series of Monosaccharide–Fipronil Conjugates and Their Phloem Mobility
  作者：Jian-Guo Yuan、Han-Xiang Wu、Meng-Ling Lu、Gao-Peng Song、Han-Hong Xu

  DOI：10.1021/jf400888c

  日期：2013.5.8

  To test the effect of adding different monosaccharide groups to a non-phloem-mobile insecticide on the phloem mobility of the insecticide, a series of conjugates of different monosaccharides and fipronil were synthesized using the trichloroacetimidate method. Phloem mobility tests in castor bean (Ricinus communis L.) seedlings indicated that the phloem mobility of these conjugates varied markedly. L-Rhamnose fipronil and D-fucose fipronil displayed the highest phloem mobility among all of the tested conjugates. Conjugating hexose, pentose, or deoxysugar to fipronil through an O-glycosidic linkage can confer phloem mobility to fipronil in R. communis L. effectively, while the -OH orientation of the monosaccharide substantially affected the phloem mobility of the conjugates.
• Paulsen, Hans; Meinjohanns, Ernst; Reck, Folkert, Liebigs Annalen der Chemie, 1993, # 7, p. 737 - 750
  作者：Paulsen, Hans、Meinjohanns, Ernst、Reck, Folkert、Brockhausen, Inka

  DOI：——

  日期：——