(1R,2S,3R,4S)-1-azido-4-(2'-furyl)-2,3-[(dimethylmethylene)dioxy]cyclopentane | 225226-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,4S)-1-azido-4-(2'-furyl)-2,3-[(dimethylmethylene)dioxy]cyclopentane
• 英文别名: (3aS,4R,6S,6aR)-4-azido-6-(furan-2-yl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole
• CAS: 225226-78-8
• 化学式: C₁₂H₁₅N₃O₃
• 分子量: 249.269
• InChiKey: YURFJFYMAYXKSN-OYBPUVFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-1-azido-4-(2'-furyl)-2,3-[(dimethylmethylene)dioxy]cyclopentane 在 ruthenium trichloride sodium periodate 、 lithium aluminium tetrahydride 作用下， 生成 (3AR,4R,6R,6AS)-6-氨基-2,2-二甲基-六氢环戊二烯并[D][1,3]二氧杂环戊烯-4-基]甲醇
  参考文献：
  名称：

  Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin

  摘要：

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。

  DOI：

  10.1039/a901819k
• 作为产物：
  描述：

  Lithium;2-butyl-2-(furan-2-yl)-4,5-dimethyl-1,3-dioxa-2-boranuidacyclopentane 在 bis(triphenylphosphine)nickel(II) chloride 四氧化锇 、 N-甲基吲哚酮 、 叠氮磷酸二苯酯 、 水 、 4-甲基苯磺酸吡啶 作用下， 反应 7.0h， 生成 (1R,2S,3R,4S)-1-azido-4-(2'-furyl)-2,3-[(dimethylmethylene)dioxy]cyclopentane
  参考文献：
  名称：

  Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin

  摘要：

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。

  DOI：

  10.1039/a901819k

文献信息

• Highly Stereoselective Synthesis of Aristeromycin through Dihydroxylation of 4-Aryl-1-azido-2-cyclopentenes
  作者：Takauki Ainai、Yong-Gang Wang、Yuko Tokoro、Yuichi Kobayashi

  DOI：10.1021/jo034672u

  日期：2004.2.1

  Dihydroxylation of 4-aryl-1-azido-2-cyclopentenes 6, in which an aryl group is used as a synthetic equivalent of CH2OH, was studied to improve the low to moderate stereoselectivity previously reported for cyclopentenes 3 possessing CH2X and nitrogen atom-containing groups. 2-Furyl, Ph, and p-MeOC6H4 groups were chosen as the aryl groups. Compounds 6a-c possessing such aryl groups were prepared by CuCN-catalyzed reaction between 2-cyclopentene-1,4-diol monoacetate 9 and the corresponding Grignard reagents followed by substitution of the hydroxyl group with (PhO)(2)P(=O)N-3. The desired diols 7a-c were obtained with higher selectivities of > 7:1 when dihydroxylation of 6a-c was carried out at 0degreesC with OsO4 (catalyst) and NMO in a mixed solvent of MeCN, THF, t-BuOH, and H2O. Among them, the furyl compound recorded the highest selectivity of 14:1. The furyl and azido groups on diol 7a were converted into hydroymethyl and adeninyl groups, respectively, to produce acetonide 2, which upon hydrolysis affords aristeromycin 1.