phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside | 183075-04-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside
• 英文别名: (2R,3S)-2-(hydroxymethyl)-5-phenylsulfanyloxolan-3-ol
• CAS: 183075-04-9
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: JUQZRMFPMKBTOJ-MTULOOOASA-N

物化性质

• 沸点：
  433.5±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 Dowex ^R 50W 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 6-methyl-2,4-bis(trimethylsiloxy)pyrimidine 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成 司他夫定
  参考文献：
  名称：

  从2-脱氧核糖轻松合成2'，3'-不饱和核苷

  摘要：

  描述了一种从2-脱氧核糖开始合成2'，3'-不饱和核苷的直接方法。这种新颖的途径涉及两种新方法：（1）通过2-脱氧核糖和苯硫酚的直接缩合制备2-脱氧-1-硫代呋喃核糖苷，（2）通过2,3-不饱和的1-硫喷呋喃糖苷与嘧啶碱基的直接偶联形成核苷骨架。

  DOI：

  10.1016/0040-4039(96)01293-2
• 作为产物：
  描述：

  2-脱氧-D-核糖 、 苯硫酚 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside
  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.
• Facile synthesis of 2′,3′-unsaturated nucleosides from 2-deoxyribose
  作者：Keiko Sujino、Tomoyasu Yoshida、Hideyuki Sugimura

  DOI：10.1016/0040-4039(96)01293-2

  日期：1996.8

  A straightforward approach for the synthesis of 2′,3′-unsaturated nucleosides starting from 2-deoxyribose is described. This novel route involves two new methods; (1) preparation of 2-deoxy-1-thioribofuranoside by direct condensation of 2-deoxyribose and thiophenol, (2) formation of the nucleoside skeleton by the direct coupling of 2,3-unsaturated 1-thiopentofuranoside with pyrimidine bases.

  描述了一种从2-脱氧核糖开始合成2'，3'-不饱和核苷的直接方法。这种新颖的途径涉及两种新方法：（1）通过2-脱氧核糖和苯硫酚的直接缩合制备2-脱氧-1-硫代呋喃核糖苷，（2）通过2,3-不饱和的1-硫喷呋喃糖苷与嘧啶碱基的直接偶联形成核苷骨架。