(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite | 637004-85-4

• 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)benzyl N,N-diisopropyl phosphoramidite
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxyoxan-2-yl]methyl acetate
• CAS: 637004-85-4
• 化学式: C₂₇H₄₀NO₁₁P
• 分子量: 585.588
• InChiKey: ZNNXPYKYUBBXRM-NRZRJTNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite 在 palladium on activated charcoal 四氮唑 、 氢气 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.0h， 生成 Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-hydroxy-propionylamino)-3-hydroxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-hydroxy-phosphoryloxy}-tetrahydro-pyran-4-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 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl 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

文献信息

• Chemical Synthesis of α-<scp>d</scp>-Mannosylphosphate Serine Derivatives: A New Class of Synthetic Glycopeptides
  作者：Geert-Jan Boons、Galal Elsayed

  DOI：10.1055/s-2003-40344

  日期：——

  α-d-Mannosylphosphate serine derivatives were conveniently synthesized by reaction of benzyl or cyanoethyl phosphochloroamidites with 2,3,4,6-tetra-O-acetyl-d-mannose to give intermediate α-mannosyl phosphoramidites, which were successfully reacted with properly protected serine derivatives in the presence of 1H-tetrazole to give phosphite triesters which could be oxidized to phosphotriesters using t-BuOOH.

  通过苄基或氰基乙基磷酰氯酰胺与 2,3,4,6- O-四乙酰基-d-甘露糖反应得到中间体δ-甘露糖基磷酰胺，然后与适当保护的丝氨酸衍生物在 1H- 四氮唑存在下反应得到亚磷酸三酯，再用 t-BuOOH 将其氧化为磷酯，从而方便地合成了δ-d-甘露糖基磷酸丝氨酸衍生物。