methyl (allyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate | 819814-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (allyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
• 英文别名: methyl (2R,4S,5S,6R)-5-acetamido-6-[(1S,2R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]-3-hydroxypropyl]-4-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enoxyoxane-2-carboxylate
• CAS: 819814-51-2
• 化学式: C₃₃H₆₇NO₉Si₃
• 分子量: 706.153
• InChiKey: VRYHWAVKOPIRBN-NUWJCFCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (allyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 在 吡啶 、 三乙胺三氧化硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl (allyl 5-acetamido-4-acetyl-7,8-di-O-tert-butyldimethylsilyl-3,5-dideoxy-9-O-sulfo-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
  参考文献：
  名称：

  Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions

  摘要：

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.095
• 作为产物：
  描述：

  Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 四溴化碳 、 lutidine 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl (allyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
  参考文献：
  名称：

  Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions

  摘要：

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.095