p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-Obenzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-β-D-glucopyranoside | 1372659-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-Obenzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-β-D-glucopyranoside
• CAS: 1372659-88-5
• 化学式: C₄₃H₅₅NO₁₃Si
• 分子量: 821.994
• InChiKey: MEDPJCZPRVIUTN-BMJVYHSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  147.7
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-Obenzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-β-D-glucopyranoside 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-O-benzyl-β-D-glucopyranosyluronate)-β-D-glucopyranoside
  参考文献：
  名称：

  Strict Stereocontrol by 2,4-O-Di-tert-butylsilylene Group on β-Glucuronylations

  摘要：

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.

  DOI：

  10.1021/ol300634x
• 作为产物：
  描述：

  methyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranosyluronate) 在 二苯基亚砜 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-Obenzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-β-D-glucopyranoside
  参考文献：
  名称：

  Strict Stereocontrol by 2,4-O-Di-tert-butylsilylene Group on β-Glucuronylations

  摘要：

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.

  DOI：

  10.1021/ol300634x