1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-β-D-ribofuranosyl]thymine | 1235869-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-β-D-ribofuranosyl]thymine
• 英文别名: 1-[(4aR,6R,7R,7aR)-2,2-ditert-butyl-7-iodo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1235869-79-0
• 化学式: C₁₈H₂₉IN₂O₅Si
• 分子量: 508.429
• InChiKey: PHKPLTXUUFPHKD-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-β-D-ribofuranosyl]thymine 在 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以84%的产率得到3',5'-O-(Di-tert-butylsilanediyl)thymidine
  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：

  1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-D-erythro-pent-1-enitol 、 O,O-二(三甲基甲硅烷基)胸苷 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 以76%的产率得到1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-β-D-ribofuranosyl]thymine
  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