methyl 5-azido-2,5-dideoxy-D-erythro-pentofuranoside | 170553-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-azido-2,5-dideoxy-D-erythro-pentofuranoside
• 英文别名: 2,5-dideoxy-1-O-methyl-5-azido-D-ribofuranose；methyl 5-azido-2,5-dideoxy-D-ribofuranoside；2′-deoxy-1′-O-methyl-5′-azido-D-ribofuranose；(2R,3S)-2-(azidomethyl)-5-methoxyoxolan-3-ol
• CAS: 170553-85-2
• 化学式: C₆H₁₁N₃O₃
• 分子量: 173.172
• InChiKey: NLMMFSMYHJUSMB-YRZWDFBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-azido-2,5-dideoxy-D-erythro-pentofuranoside 在 15-冠醚-5 吡啶 、 叠氮化锂 、 水 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 methyl (3S,4R)-3,5-diazido-2,3,5-trideoxy-α,β-pentofuranoside
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 叠氮化锂 、 硫酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 methyl 5-azido-2,5-dideoxy-D-erythro-pentofuranoside
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175

文献信息

• Functionalized C-nucleosides as remarkable RNA binders: targeting of prokaryotic ribosomal A-site RNA
  作者：Jean-Patrick Joly、Marc Gaysinski、Lorena Zara、Maria Duca、Rachid Benhida

  DOI：10.1039/c9cc04915k

  日期：——

  Novel C-nucleosides as selective binders of prokaryotic ribosomal A-site RNA and promising scaffolds for therapeutic RNA targeting.

  小说C-核苷酸作为选择性结合原核核糖体A位点RNA的分子和有前途的治疗RNA靶向的支架。
• 2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks
  作者：Dengjin Wang、William A. Nugent

  DOI：10.1021/jo0712143

  日期：2007.9.1

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.
• Synthesis of 3′-Amino and 5′-Amino Hydantoin 2′-Deoxynucleosides
  作者：Ahmed A. El-Barbary、Ahmed I. Khodair、Erik B. Pedersen、Claus Nielsen

  DOI：10.1080/15257779408013274

  日期：1994.3

  3'-Amino and 5'-amino derivatives of hydantoin 2'-deoxynucleosides have been prepared from the corresponding 3'-phthalimido and 5'-azido nucleosides, respectively, which in turn were prepared by condensation of appropriate sugars with 5-benzylidenehydantoin. The amino nucleosides were tested for their potential activity against HIV and HSV.
• Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway
  作者：Daniel Koth、Andrea Fiedler、Sandy Scholz、Michael Gottschaldt

  DOI：10.1080/07328300701540175

  日期：2007.9

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.