methyl (E)-2,3,4-tri-O-benzyl-6-deoxy-6-ethoxysulfonylmethylene-α-D-mannopyranoside | 1097188-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (E)-2,3,4-tri-O-benzyl-6-deoxy-6-ethoxysulfonylmethylene-α-D-mannopyranoside
• CAS: 1097188-25-4
• 化学式: C₃₁H₃₆O₈S
• 分子量: 568.688
• InChiKey: BKKIOBCMAUWXEK-SHVBSOCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-2,3,4-tri-O-benzyl-6-deoxy-6-ethoxysulfonylmethylene-α-D-mannopyranoside 、 四丁基碘化铵 以 丙酮 为溶剂， 以81%的产率得到methyl (E)-2,3,4-tri-O-benzyl-6-deoxy-6-hydroxysulfonylmethylene-α-D-mannopyranoside N-tetrabutylammonium salt
  参考文献：
  名称：

  Synthesis of new sulfonate and phosphonate derivatives for cation-independent mannose 6-phosphate receptor targeting

  摘要：

  The cation-independent mannose 6-phosphate receptor (CI-M6PR) is essential for the endocytosis of proteins bearing the mannose 6-phosphate (M6P) recognition marker. This study described the synthesis of M6P and M6S analogs presenting greater affinity for CI-M6PR than their natural compounds. Moreover, the finding of their lack of cytotoxicity for human cells and of their increased stability in human serum supports the high potential of these isosteric derivatives in therapies requiring CI-M6PR targeting. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.101
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 、 ethyl (diethoxyphosphoryl)methanesulfonate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以694 mg的产率得到methyl (E)-2,3,4-tri-O-benzyl-6-deoxy-6-ethoxysulfonylmethylene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of new sulfonate and phosphonate derivatives for cation-independent mannose 6-phosphate receptor targeting

  摘要：

  The cation-independent mannose 6-phosphate receptor (CI-M6PR) is essential for the endocytosis of proteins bearing the mannose 6-phosphate (M6P) recognition marker. This study described the synthesis of M6P and M6S analogs presenting greater affinity for CI-M6PR than their natural compounds. Moreover, the finding of their lack of cytotoxicity for human cells and of their increased stability in human serum supports the high potential of these isosteric derivatives in therapies requiring CI-M6PR targeting. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.101