6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone | 200728-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone
• 英文别名: (5S)-5-[(1R)-2-azido-1-hydroxyethyl]oxolan-2-one
• CAS: 200728-42-3
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: ZLJGVKSWKYTPGB-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到(5S,6R)-5,6-二羟基-2-氮杂环庚酮
  参考文献：
  名称：

  Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam

  摘要：

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00319-5
• 作为产物：
  描述：

  (5S,1'S)-5-(2'-bromo-1'-hydroxy)ethyl-4,5-dihydro-2-(3H)-furanone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone
  参考文献：
  名称：

  3′-Modified Nucleotides for DNA Sequencing Without Gel Electrophoresis

  摘要：

  Dibenzyl-3'-O-[(6-azido-2,3,6-trideoxy-4,5-di-O-benzyl) hexanoyl] thymidine 5'-yl phosphate 8a was prepared. Catalytic hydrogenolysis removed only the benzyl esters and reduced the azido group. When the benzyl ethers were replaced by p-phenylbenzyl or allyl ethers, their deprotection also failed.

  DOI：

  10.1080/07328319708006271

文献信息

• 3′-Modified Nucleotides for DNA Sequencing Without Gel Electrophoresis
  作者：Isabelle Rasolonjatovo、Catherine Guerreiro、Robert S. Sarfati

  DOI：10.1080/07328319708006271

  日期：1997.7

  Dibenzyl-3'-O-[(6-azido-2,3,6-trideoxy-4,5-di-O-benzyl) hexanoyl] thymidine 5'-yl phosphate 8a was prepared. Catalytic hydrogenolysis removed only the benzyl esters and reduced the azido group. When the benzyl ethers were replaced by p-phenylbenzyl or allyl ethers, their deprotection also failed.
• Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam
  作者：Michaela Hamernı́ková、Svetlana Pakhomova、Jaroslav Havlı́ček、Hana Votavová、Karel Kefurt

  DOI：10.1016/s0008-6215(99)00319-5

  日期：2000.3

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.