benzyl 2-cyanoethyl [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl phosphate | 1200440-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-cyanoethyl [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl phosphate
• CAS: 1200440-76-1
• 化学式: C₃₈H₄₂NO₉P
• 分子量: 687.727
• InChiKey: UOJXNEDKLDCSAJ-VYDJWYPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2-cyanoethyl [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl phosphate 、 四丁基氢氧化铵 以 二氯甲烷 、 水 为溶剂， 以99%的产率得到benzyl [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl phosphate;tetrabutylazanium
  参考文献：
  名称：

  Highly Stereoselective Synthesis of α-d-Mannopyranosyl Phosphosugars

  摘要：

  alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

  DOI：

  10.1021/jo902254w
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 O-benzyl-O-β-cyanoethyl-N,N-diisopropylphosphoramidite 在 benzimidazolium triflate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到benzyl 2-cyanoethyl [(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl phosphate
  参考文献：
  名称：

  Highly Stereoselective Synthesis of α-d-Mannopyranosyl Phosphosugars

  摘要：

  alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

  DOI：

  10.1021/jo902254w

文献信息

• Highly Stereoselective Synthesis of α-<scp>d</scp>-Mannopyranosyl Phosphosugars
  作者：David Crich、Sébastien Picard

  DOI：10.1021/jo902254w

  日期：2009.12.18

  alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.