Thiophosphoric acid O,O'-dimethyl ester O''-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl) ester | 212119-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Thiophosphoric acid O,O'-dimethyl ester O''-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl) ester
• CAS: 212119-72-7
• 化学式: C₃₆H₄₁O₈PS
• 分子量: 664.756
• InChiKey: XXQDPFFTMSJESQ-DQROVBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 Thiophosphoric acid O,O'-dimethyl ester O''-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl) ester 在 4 Angstroem MS 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以78%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl α-D-mannopyranosyl) α-D-glucopyranoside
  参考文献：
  名称：

  Preparation of Glycosyl Dimethylthiophosphates and Their Application as Glycosyl Donors

  摘要：

  Benzyl- and acetyl-protected glycosyl dimethylthiophosphates were readily prepared from corresponding l-hydroxyl sugars in good yield, and acted as very stable and efficient glycosyl donors in the construction of glycosidic bonds in the presence of various promoters.

  DOI：

  10.1080/07328309808002336
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannopyranose 、 二甲基硫代磷酰氯 在 正丁基锂 作用下， 生成 Thiophosphoric acid O,O'-dimethyl ester O''-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl) ester
  参考文献：
  名称：

  Preparation of Glycosyl Dimethylthiophosphates and Their Application as Glycosyl Donors

  摘要：

  Benzyl- and acetyl-protected glycosyl dimethylthiophosphates were readily prepared from corresponding l-hydroxyl sugars in good yield, and acted as very stable and efficient glycosyl donors in the construction of glycosidic bonds in the presence of various promoters.

  DOI：

  10.1080/07328309808002336