(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite | 849063-81-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite
• CAS: 849063-81-6
• 化学式: C₂₆H₄₇N₂O₁₀P
• 分子量: 578.64
• InChiKey: IUKXTTFRCSCABV-PUHDZGQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  130.14
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite 在 palladium on activated charcoal 四氮唑 、 氢气 、 一水合肼 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 68.0h， 生成 Phosphoric acid (S)-2-[(S)-2-((S)-2-acetylamino-3-hydroxy-propionylamino)-3-hydroxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethyl ester (2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Synthesis of Proteophosphoglycans of Leishmania major and Leishmania mexicana

  摘要：

  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.

  DOI：

  10.1021/jo048443z
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 、 双二异丙基氨基氯化磷 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以72%的产率得到(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite
  参考文献：
  名称：

  Synthesis of Proteophosphoglycans of Leishmania major and Leishmania mexicana

  摘要：

  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.

  DOI：

  10.1021/jo048443z