Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-phenylsulfanyl-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester | 216776-90-8

• 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: Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-phenylsulfanyl-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 216776-90-8
• 化学式: C₄₂H₄₇ClO₁₅S
• 分子量: 859.345
• InChiKey: FEBSLUSCHHLNTF-QSQWWFHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  59.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  177.65
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-phenylsulfanyl-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 在 三氟甲磺酸 、 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 phenyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-6)-[O-(2,3,4,6-tetra-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：

  phenyl 2,4-di-O-benzyl-1-thio-α-D-mannopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-phenylsulfanyl-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
  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