tri-O-benzyl-2-azido-2-deoxy-D-mannono-1,5-lactone | 162284-48-2

• 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: tri-O-benzyl-2-azido-2-deoxy-D-mannono-1,5-lactone
• 英文别名: (3S,4R,5S,6R)-3-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one
• CAS: 162284-48-2
• 化学式: C₂₇H₂₇N₃O₅
• 分子量: 473.528
• InChiKey: JZVINQNAXZEQKZ-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tri-O-benzyl-2-azido-2-deoxy-D-mannono-1,5-lactone 在 三乙基硅烷 、 正丁基锂 、 cerium(III) chloride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-talo-oct-1-ynitol
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m
• 作为产物：
  描述：

  2-deoxy-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 生成 tri-O-benzyl-2-azido-2-deoxy-D-mannono-1,5-lactone
  参考文献：
  名称：

  Electrophilic azidation of 2-deoxy-aldono-1,5-lactones: an alternative route to 2-azido-2-deoxy-aldopyranoses

  摘要：

  三-O-苄基-2-脱氧-D-半乳糖醛-1,5-内酯3与三异丙基苯磺酰叠氮化物的电亲核叠氮化反应，随后使用二异丁基铝氢化物进行选择性还原，得到了三-O-苄基-2-叠氮-2-脱氧-D-半乳糖吡喃糖5，产率为80%，而对2-脱氧-D-葡萄糖醛-1,5-内酯衍生物8进行相同的反应顺序仅得到三-O-苄基-2-叠氮-2-脱氧-D-甘露糖吡喃糖10，产率为65%。

  DOI：

  10.1039/c39950000221

文献信息

• Electrophilic azidation of 2-deoxy-aldono-1,5-lactones: an alternative route to 2-azido-2-deoxy-aldopyranoses
  作者：Fran�ois-Yves Dupradeau、Sen-itiroh Hakomori、Tatsushi Toyokuni

  DOI：10.1039/c39950000221

  日期：——

  Electrophilic azidation of tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone 3 with triisopropylphenylsulfonyl azide, followed by selective reduction with diisobutylaluminium hydride, yielded tri-O-benzyl-2-azido-2-deoxy-D-galactopyranose 5 as the sole product in 80% yield, while the same sequence of reactions with the 2-deoxy-glucono-1,5-lactone derivative 8 afforded only tri-O-benzyl-2-azido-2-deoxy-D-mannopyranose 10 in 65% yield.

  三-O-苄基-2-脱氧-D-半乳糖醛-1,5-内酯3与三异丙基苯磺酰叠氮化物的电亲核叠氮化反应，随后使用二异丁基铝氢化物进行选择性还原，得到了三-O-苄基-2-叠氮-2-脱氧-D-半乳糖吡喃糖5，产率为80%，而对2-脱氧-D-葡萄糖醛-1,5-内酯衍生物8进行相同的反应顺序仅得到三-O-苄基-2-叠氮-2-脱氧-D-甘露糖吡喃糖10，产率为65%。
• Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (<i>C</i>-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling
  作者：Alessandro Dondoni、Giandomenico Mariotti、Alberto Marra

  DOI：10.1021/jo020054m

  日期：2002.6.1

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.
• Electrophilic Azidation for Stereoselective Synthesis of 2-Azido-2-deoxyaldono-1,5-lactones
  作者：J. S. Dileep Kumar、François-Yves Dupradeau、M. Jane Strouse、Michael E. Phelps、Tatsushi Toyokuni

  DOI：10.1021/jo005728c

  日期：2001.5.1