(2R)-2-azidohexadecyl-3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside | 402923-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-azidohexadecyl-3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside
• CAS: 402923-22-2
• 化学式: C₃₂H₅₄N₄O₁₀
• 分子量: 654.802
• InChiKey: PLCSKMGEMSOVGY-WFSCRAEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  46.0
• 可旋转键数：
  24.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  184.45
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-azidohexadecyl-3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside 在 四(三苯基膦)钯 丙二酸二甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (2R)-2-azidohexadecyl-3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides

  摘要：

  Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air \ water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta -D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air \ water interface; their pi -A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00255-5
• 作为产物：
  描述：

  1,2-环氧十六烷 在 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 偶氮二甲酸二异丙酯 、 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (2R)-2-azidohexadecyl-3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides

  摘要：

  Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air \ water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta -D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air \ water interface; their pi -A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00255-5