(3,4,6-tri-O-acetyl-2-acetamido-α-D-glucopyranosyl) bis-N,N-diisopropyl phosphoramidite | 849063-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-acetyl-2-acetamido-α-D-glucopyranosyl) bis-N,N-diisopropyl phosphoramidite
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-bis[di(propan-2-yl)amino]phosphanyloxyoxan-2-yl]methyl acetate
• CAS: 849063-82-7
• 化学式: C₂₆H₄₈N₃O₉P
• 分子量: 577.656
• InChiKey: CAKNLSXVRYWELQ-ZFXZZAOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3,4,6-tri-O-acetyl-2-acetamido-α-D-glucopyranosyl) bis-N,N-diisopropyl phosphoramidite 在 四氮唑 、 palladium 10% on activated carbon 、 氢气 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 46.0h， 生成 propyl 6-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-phosphonato-1-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis of N-Linked Glycans Carrying Both Mannose-6-phosphate and GlcNAc-Mannose-6-phosphate Motifs

  摘要：

  Mannose-6-phosphate (M6P) containing N-linked glycans are the essential targeting signals for hydrolases sorting in eukaryotic cells. To facilitate their structural and binding analyses, a highly efficient and convergent method has been developed to prepare complex N-linked glycans with well-defined M6P and N-acetylglucosamine (GlcNAc)-M6P motifs, a newly identified binding element for M6P receptors. The GlcNAc-M6P motif was stereoselectively installed at the late stage of the synthesis. Sequential deprotection of benzyl and acetate groups provided the fully deprotected N-glycans in excellent yield.

  DOI：

  10.1021/jo2010999
• 作为产物：
  描述：

  双二异丙基氨基氯化磷 、 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(3,4,6-tri-O-acetyl-2-acetamido-α-D-glucopyranosyl) bis-N,N-diisopropyl phosphoramidite
  参考文献：
  名称：

  Synthesis of Cell-Permeable N-Acetylhexosamine 1-Phosphates

  摘要：

  DOI：

  10.1021/acs.joc.1c01781

文献信息

• Synthesis of Proteophosphoglycans of <i>Leishmania </i><i>m</i><i>ajor</i> and <i>Leishmania </i><i>m</i><i>exicana</i>
  作者：Debatosh Majumdar、Galal A. Elsayed、Therese Buskas、Geert-Jan Boons

  DOI：10.1021/jo048443z

  日期：2005.3.1

  A novel approach for the synthesis of various fragments of proteophosphoglycans from Leishmania major and Leishmania mexicana proteophosphoglycans has been developed. These compounds have been obtained by coupling alpha-mannosyl and alpha-acetyl-glucosamine phosphoramidite derivatives with the serine hydroxyl of various amino acids and peptides to give, after oxidation with tert-BuOOH, phosphotriesters exclusively as alpha-anomers in good yield. The resulting compounds could be deblocked using conventional methods. Glycophosphorylation of preassembled and properly protected peptides was found to be more efficient for the preparation of proteophosphoglycan fragments than a building block approach strategy using a phosphoglycosylserine derivative.