N4-acetyl-1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-1-C-(triethyl-silyloxymethyl)-β-D-ribofuranosyl]cytosine | 1235870-16-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N4-acetyl-1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-1-C-(triethyl-silyloxymethyl)-β-D-ribofuranosyl]cytosine
• CAS: 1235870-16-2
• 化学式: C₂₆H₄₆IN₃O₆Si₂
• 分子量: 679.743
• InChiKey: PSVLGURPKCMZRV-RKCWLVDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  100.91
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N4-acetyl-1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-1-C-(triethyl-silyloxymethyl)-β-D-ribofuranosyl]cytosine 在 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 0.17h， 以95%的产率得到N4-acetyl-1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-1-C-(triethylsilyloxy-methyl)-β-D-ribofuranosyl]cytosine
  参考文献：
  名称：

  Electrophilic glycosidation employing 3,5-O-(di-tert-butylsilylene)-erythro-furanoid glycal leads to exclusive formation of the β-anomer: synthesis of 2′-deoxynucleosides and its 1′-branched analogues

  摘要：

  Stereoselectivity in N-iodosuccimide (NIS)-mediated electrophilic glycosidation was examined by employing 2,4-bis-O-(trimethylsilyl)thymine and three different silyl-protected erythro-furanoid glycals 12, 16, and 18. As a result, it was found that 3,5-O-(di-t-butylsilylene)-protected 18 gave only the beta-anomer (21). The remarkable stereoselectivity observed by employing 18 is discussed on the basis of its X-ray crystallographic analysis. 1-Substituted glycals gave the corresponding beta-anomer, again exclusively, to provide access to 1'-branched 2'-deoxynucleosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.043
• 作为产物：
  描述：

  N4-乙酰胞嘧啶 、 1,4-anhydro-2-deoxy-3,5-di-O-(di-tert-butylsilylene)-1-C-(triethylsilyloxy-methyl)-D-erythro-pent-1-enitol 在 N,O-双三甲硅基乙酰胺 、 N-碘代丁二酰亚胺 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 12.0h， 以84%的产率得到N4-acetyl-1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-1-C-(triethyl-silyloxymethyl)-β-D-ribofuranosyl]cytosine
  参考文献：
  名称：

  Electrophilic glycosidation employing 3,5-O-(di-tert-butylsilylene)-erythro-furanoid glycal leads to exclusive formation of the β-anomer: synthesis of 2′-deoxynucleosides and its 1′-branched analogues

  摘要：

  Stereoselectivity in N-iodosuccimide (NIS)-mediated electrophilic glycosidation was examined by employing 2,4-bis-O-(trimethylsilyl)thymine and three different silyl-protected erythro-furanoid glycals 12, 16, and 18. As a result, it was found that 3,5-O-(di-t-butylsilylene)-protected 18 gave only the beta-anomer (21). The remarkable stereoselectivity observed by employing 18 is discussed on the basis of its X-ray crystallographic analysis. 1-Substituted glycals gave the corresponding beta-anomer, again exclusively, to provide access to 1'-branched 2'-deoxynucleosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.043