1,4-anhydro-2-deoxy-3,5-bis-O-(di-tert-butylsilylene)-1-C-methyl-D-erythro-pent-1-enitol | 1235869-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 1,4-anhydro-2-deoxy-3,5-bis-O-(di-tert-butylsilylene)-1-C-methyl-D-erythro-pent-1-enitol
• 英文别名: (4aR,7aS)-2,2-ditert-butyl-6-methyl-4a,7a-dihydro-4H-furo[3,2-d][1,3,2]dioxasiline
• CAS: 1235869-86-9
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: AMPNRVKGOMKIOD-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-3,5-bis-O-(di-tert-butylsilylene)-1-C-methyl-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57%的产率得到1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-1-C-methyl-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
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-D-erythro-pent-1-enitol 、 碘甲烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 、 六甲基磷酰三胺 为溶剂， 反应 1.0h， 以56%的产率得到1,4-anhydro-2-deoxy-3,5-bis-O-(di-tert-butylsilylene)-1-C-methyl-D-erythro-pent-1-enitol
  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

文献信息

• 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
  作者：Kazuhiro Haraguchi、Kiju Konno、Kaori Yamada、Yasuyuki Kitagawa、Kazuo T. Nakamura、Hiromichi Tanaka

  DOI：10.1016/j.tet.2010.04.043

  日期：2010.6

  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.