phenyl 2,4-di-O-benzyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside | 216776-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4-di-O-benzyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5S,6R)-4-hydroxy-3,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl 2-chloroacetate
• CAS: 216776-70-4
• 化学式: C₂₈H₂₉ClO₆S
• 分子量: 529.054
• InChiKey: OHAOEBJKPNCCHE-AGKKLSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2,4-di-O-benzyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside 在 三氟甲磺酸 、 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A Short, Efficient Synthesis of the Octamannan Residue of High Mannose Type Sugar Chains

  摘要：

  An efficient route for the synthesis of octamannan 1, found in high mannose type sugar chains, is described. To construct octasaccharide 1 by as few synthetic steps as possible, we employed a chemoenzymatic strategy: the enzymatic synthesis of oligosaccharide blocks using glycosidases followed by chemical coupling to form a branched structure. By use of this methodology, many synthetic steps were eliminated and 1 was easily synthesized.

  DOI：

  10.1080/07328309808001897
• 作为产物：
  描述：

  氯乙酸酐 、 phenyl 2,4-di-O-benzyl-1-thio-α-D-mannopyranoside 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 以82%的产率得到phenyl 2,4-di-O-benzyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A Short, Efficient Synthesis of the Octamannan Residue of High Mannose Type Sugar Chains

  摘要：

  An efficient route for the synthesis of octamannan 1, found in high mannose type sugar chains, is described. To construct octasaccharide 1 by as few synthetic steps as possible, we employed a chemoenzymatic strategy: the enzymatic synthesis of oligosaccharide blocks using glycosidases followed by chemical coupling to form a branched structure. By use of this methodology, many synthetic steps were eliminated and 1 was easily synthesized.

  DOI：

  10.1080/07328309808001897

文献信息

• Construction of a High‐Mannose‐Type Glycan Library by a Renewed Top‐Down Chemo‐Enzymatic Approach
  作者：Kohki Fujikawa、Akihiko Koizumi、Masakazu Hachisu、Akira Seko、Yoichi Takeda、Yukishige Ito

  DOI：10.1002/chem.201405781

  日期：2015.2.16

  method for the construction of a high‐mannose‐type glycan library by systematic chemo‐enzymatic trimming of a single Man9‐based precursor was developed. It consists of the chemical synthesis of a non‐natural tridecasaccharide precursor, the orthogonal demasking of the non‐reducing ends, and trimming by glycosidases, which enabled a comprehensive synthesis of high‐mannose‐type glycans in their mono‐

  通过系统化学修饰单个基于Man9的前体，开发了一种构建高甘露糖型聚糖文库的综合方法。它包括非天然十三糖前体的化学合成，非还原末端的正交脱模以及糖苷酶的修饰，从而能够以单糖或非糖基化形式全面合成高甘露糖型聚糖。 。它使用葡萄糖，异亚丙基和N-乙酰氨基葡萄糖基团分别阻断A-，B-和C-臂。对前体进行系统修剪后，获得了37个高甘露糖型聚糖。人类重组N的酶促活性证明了该方法的强大功能-乙酰氨基葡萄糖氨基转移酶-I对M7-M3聚糖的作用，阐明了在高甘露糖型聚糖的情况下底物的特异性。
• Top-Down Chemoenzymatic Approach to a High-Mannose-Type Glycan Library: Synthesis of a Common Precursor and Its Enzymatic Trimming
  作者：Akihiko Koizumi、Ichiro Matsuo、Maki Takatani、Akira Seko、Masakazu Hachisu、Yoichi Takeda、Yukishige Ito

  DOI：10.1002/anie.201301613

  日期：2013.7.15

  From the stacks: A novel method for construction of a high‐mannose‐type glycan library by systematic enzymatic trimming of a single synthetic Man9‐based precursor was developed. Efficient chemical synthesis of the tetradecasaccharide common precursor and orthogonal enzymatic trimming to obtain all M8‐9 and G1M8‐9 derivatives was demonstrated. G=glucose, M=mannose.

  从堆栈中：开发了一种通过对单个合成的基于Man 9的前体进行系统化酶切来构建高甘露糖型聚糖文库的新方法。证明了十四碳糖共同前体的有效化学合成和正交酶修整可得到所有M 8-9和G 1 M 8-9衍生物。G ＝葡萄糖，M ＝甘露糖。
• Comprehensive synthesis of ER related high-mannose-type sugar chains by convergent strategy
  作者：Ichiro Matsuo、Kiichiro Totani、Atsushi Tatami、Yukishige Ito

  DOI：10.1016/j.tet.2006.06.045

  日期：2006.8

  Systematic synthesis of high-mannose-type sugar chains of asparagine-linked glycoproteins is described. To construct the target sugar chains, we employed the convergent route, using three oligosaccharide components, the common hexasaccharide, branched tri-, tetra- and pentasaccharides, and mono-, di-, and triglucosyl fragments. Construction of the β-mannoside linkage was performed using p-methoxybenzyl-assisted

  描述了天冬酰胺连接的糖蛋白的高甘露糖型糖链的系统合成。为了构建目标糖链，我们采用了收敛途径，使用了三种低聚糖成分：普通六糖，支链三糖，四糖和五糖以及单糖，二糖和三糖基片段。使用p进行β-甘露糖苷键的构建-甲氧基苄基辅助的分子内糖苷配基递送。将六糖片段与支链甘露寡糖供体（例如M5，M4B，M4C和M3）偶联，分别得到十一碳糖（M9），十糖（M8B和M8C）和九糖（M7）。结合它们的单，二和三葡萄糖基片段分别得到十四碳糖（G3M9），十三碳糖（G2M9），十二碳糖（G1M9），十一碳糖（G1M8B和G1M8C）和十碳糖（G1M7）。