methyl (phenyl 5-tert-butoxycarbonylamino-8,9-isopropylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate | 1046456-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 5-tert-butoxycarbonylamino-8,9-isopropylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate
• CAS: 1046456-65-8
• 化学式: C₂₄H₃₅NO₉S
• 分子量: 513.609
• InChiKey: UMOHKYUJJPBIOA-VREOXNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132.78
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 5-tert-butoxycarbonylamino-8,9-isopropylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 以88%的产率得到methyl (phenyl 5-amino-5-N,7-O-carbonyl-8,9-isopropylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate
  参考文献：
  名称：

  Sialylation reactions with 5-N,7-O-carbonyl-protected sialyl donors: unusual stereoselectivity with nitrile solvent assistance

  摘要：

  A 5-N,7-O-carbonyl-protected sialyl donor was synthesized, and, unexpectedly, this donor showed beta-selectivity (alpha/beta = 1/2.4-1/20) on coupling with sugar acceptors in acetonitrile upon treatment with various promoter systems. For the coupling reaction in dichloromethane, a modified Ellervik's method (IBr and AgClO4 center dot H2O) was highly effective in activating the 5-N,7-O-carbonyl donor, providing moderate alpha-selectivity (alpha/beta = similar to 1.8/1). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.005
• 作为产物：
  描述：

  methyl (phenyl 5-tert-butoxycarbonylamino-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate 、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以96%的产率得到methyl (phenyl 5-tert-butoxycarbonylamino-8,9-isopropylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)uronate
  参考文献：
  名称：

  Sialylation reactions with 5-N,7-O-carbonyl-protected sialyl donors: unusual stereoselectivity with nitrile solvent assistance

  摘要：

  A 5-N,7-O-carbonyl-protected sialyl donor was synthesized, and, unexpectedly, this donor showed beta-selectivity (alpha/beta = 1/2.4-1/20) on coupling with sugar acceptors in acetonitrile upon treatment with various promoter systems. For the coupling reaction in dichloromethane, a modified Ellervik's method (IBr and AgClO4 center dot H2O) was highly effective in activating the 5-N,7-O-carbonyl donor, providing moderate alpha-selectivity (alpha/beta = similar to 1.8/1). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.005