5-O-(tert-butyldimethylsilyl)-1-β-<5-<2,4-di(tert-butoxy)pyrimidinyl>>-1,4-dideoxy-2',3'-O-isopropylidene-1,4-imino-L-lyxitol | 214956-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(tert-butyldimethylsilyl)-1-β-<5-<2,4-di(tert-butoxy)pyrimidinyl>>-1,4-dideoxy-2',3'-O-isopropylidene-1,4-imino-L-lyxitol
• 英文别名: [(3aS,4R,6S,6aR)-4-[2,4-bis[(2-methylpropan-2-yl)oxy]pyrimidin-5-yl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 214956-66-8
• 化学式: C₂₆H₄₇N₃O₅Si
• 分子量: 509.762
• InChiKey: ZWTCNXSRYFQVOZ-NMLBUPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-(tert-butyldimethylsilyl)-1-β-<5-<2,4-di(tert-butoxy)pyrimidinyl>>-1,4-dideoxy-2',3'-O-isopropylidene-1,4-imino-L-lyxitol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到1,4-dideoxy-1,4-imino-1-β-(5-uracilyl)-L-lyxitol hydrochloride
  参考文献：
  名称：

  Synthesis and Properties of C-Azalyxonucleosides

  摘要：

  1-beta-(4-Imidazoyl)- and 1-beta-(5-uracilyl)-1,4-dideoxy-1,4-imino-L-lyxitols were synthesized stereoselectively via a sequential procedure by the addition of the corresponding metal salts of heterocycles, Swern oxidation, reductive aminocyclization, and deprotection. Their structures were determined based on X-ray crystallography. From the NMR measurements of their N-acyl derivatives, two rotational isomers were observed. Their bioassay is also described.

  DOI：

  10.1021/jo980492m
• 作为产物：
  描述：

  2,4-二叔丁氧基-5-溴嘧啶 在 sodium tetrahydroborate 、 3 A molecular sieve 、 4 A molecular sieve 、 正丁基氯化镁 、 甲酸铵 、 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 反应 26.5h， 生成 5-O-(tert-butyldimethylsilyl)-1-β-<5-<2,4-di(tert-butoxy)pyrimidinyl>>-1,4-dideoxy-2',3'-O-isopropylidene-1,4-imino-L-lyxitol
  参考文献：
  名称：

  Synthesis and Properties of C-Azalyxonucleosides

  摘要：

  1-beta-(4-Imidazoyl)- and 1-beta-(5-uracilyl)-1,4-dideoxy-1,4-imino-L-lyxitols were synthesized stereoselectively via a sequential procedure by the addition of the corresponding metal salts of heterocycles, Swern oxidation, reductive aminocyclization, and deprotection. Their structures were determined based on X-ray crystallography. From the NMR measurements of their N-acyl derivatives, two rotational isomers were observed. Their bioassay is also described.

  DOI：

  10.1021/jo980492m

文献信息

• Synthesis and Properties of <i>C</i>-Azalyxonucleosides
  作者：Atsuya Momotake、Jun Mito、Kentaro Yamaguchi、Hideo Togo、Masataka Yokoyama

  DOI：10.1021/jo980492m

  日期：1998.10.1

  1-beta-(4-Imidazoyl)- and 1-beta-(5-uracilyl)-1,4-dideoxy-1,4-imino-L-lyxitols were synthesized stereoselectively via a sequential procedure by the addition of the corresponding metal salts of heterocycles, Swern oxidation, reductive aminocyclization, and deprotection. Their structures were determined based on X-ray crystallography. From the NMR measurements of their N-acyl derivatives, two rotational isomers were observed. Their bioassay is also described.