4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate | 1158796-98-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate
• 英文别名: [(4aR,6R,7R,8R,8aS)-2,2-ditert-butyl-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl] 4-oxopentanoate
• CAS: 1158796-98-5
• 化学式: C₂₉H₃₈Cl₃F₃N₂O₈Si
• 分子量: 734.069
• InChiKey: QUMFYSIJMYNTPP-OKKOYFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate 、 methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropylmethylsulfonylethoxycarbonyl-4-O-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到methyl 2,3-di-O-benzyl-6-O-perfluorooctylpropyllsulfonylethoxycarbonyl-4-O-[2,3,6-tri-O-benzoyl-4-O-{2-deoxy-4,6-di-tert-butylsilyl-3-O-levulinoyl-2-(N-trichloroacetyl)-amino-β-D-glucopyranosyl}-β-D-glucopyranosyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry

  摘要：

  The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.146
• 作为产物：
  描述：

  4,6-O-di(tert-butyl)silylidene-2-deoxy-2-trichloroacetamido-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate 、 乙酰丙酸 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate 、 4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713

文献信息

• Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry
  作者：Asghar Ali、Richard J.B.H.N. van den Berg、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. van der Marel、Jeroen D.C. Codée

  DOI：10.1016/j.tetlet.2009.02.146

  日期：2009.5

  The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies
  作者：Jasper Dinkelaar、Henrik Gold、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo9003713

  日期：2009.6.5

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.