4-pentenyl 2-amino-2-N-3-O-carbonyl-2-deoxy-4,6-di-O-acetyl-α-D-mannopyranoside | 1133982-05-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-pentenyl 2-amino-2-N-3-O-carbonyl-2-deoxy-4,6-di-O-acetyl-α-D-mannopyranoside
• 英文别名: [(3aS,4S,6R,7S,7aR)-7-acetyloxy-2-oxo-4-pent-4-enoxy-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-6-yl]methyl acetate
• CAS: 1133982-05-4
• 化学式: C₁₆H₂₃NO₈
• 分子量: 357.361
• InChiKey: KHFSEVASHDZKPZ-KHMAMNHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-戊烯-1-醇 、 4,6-di-O-acetyl-3-O-carbamoyl-D-glucal 在 dirhodium tetraacetate 、 亚碘酰苯 、 4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以72%的产率得到4-pentenyl 2-amino-2-N-3-O-carbonyl-2-deoxy-4,6-di-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Protecting Group and Solvent Control of Stereo- and Chemoselectivity in Glucal 3-Carbamate Amidoglycosylation

  摘要：

  In the Rh-2(OAC)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 40 and 60 protecting groups. Acyclic protection permits high alpha-anomer selectivity with further improvement in less polar solvents, while electron-withdrawing protecting groups limit C3-oxidized byproducts. Stereocontrol and bifurcation between alkene insertion and C3-H oxidation reflect an interplay of conformational, stereoelectronic, and inductive factors.

  DOI：

  10.1021/ol900126q

文献信息

• Protecting Group and Solvent Control of Stereo- and Chemoselectivity in Glucal 3-Carbamate Amidoglycosylation
  作者：Ritu Gupta、Kimberly M. Sogi、Sarah E. Bernard、John D. Decatur、Christian M. Rojas

  DOI：10.1021/ol900126q

  日期：2009.4.2

  In the Rh-2(OAC)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 40 and 60 protecting groups. Acyclic protection permits high alpha-anomer selectivity with further improvement in less polar solvents, while electron-withdrawing protecting groups limit C3-oxidized byproducts. Stereocontrol and bifurcation between alkene insertion and C3-H oxidation reflect an interplay of conformational, stereoelectronic, and inductive factors.