phenyl 3,4-di-O-acetyl-2,6-anhydro-1,2-dithio-D-altropyranoside | 132016-26-3

• 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 3,4-di-O-acetyl-2,6-anhydro-1,2-dithio-D-altropyranoside
• 英文别名: [(1S,4S,7R,8R)-8-acetyloxy-3-phenylsulfanyl-2-oxa-5-thiabicyclo[2.2.2]octan-7-yl] acetate
• CAS: 132016-26-3
• 化学式: C₁₆H₁₈O₅S₂
• 分子量: 354.448
• InChiKey: NCLSBNKYJXKZGD-YFVFXCHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-acetyl-2,6-anhydro-1,2-dithio-D-altropyranoside 在 N-溴代丁二酰亚胺(NBS) 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 tin(ll) chloride 作用下， 以 乙醚 为溶剂， 反应 1.67h， 生成 cyclohexyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside
  参考文献：
  名称：

  The use of 2,6-anhydro-2-thio glycopyranosyl fluoride for a highly α-stereoselective glycosylation

  摘要：

  DOI：

  10.1016/s0040-4039(00)97064-3
• 作为产物：
  描述：

  (1S,3S,4S,7S,8R)-3-Methoxy-2-oxa-5-thia-bicyclo[2.2.2]octane-7,8-diol 在 4-二甲氨基吡啶 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 phenyl 3,4-di-O-acetyl-2,6-anhydro-1,2-dithio-D-altropyranoside
  参考文献：
  名称：

  2，6-脱水-2-硫代糖用于高度立体控制的糖基化：2,6-二脱氧-α-糖苷合成的新策略

  摘要：

  通过在高度立体控制的糖基化中使用苯基2，6-脱水-1，2-二硫基-D-阿托拉糖苷作为糖基供体，开发了2，6-二脱氧-α-糖苷的新型有效合成方法。

  DOI：

  10.1016/s0040-4039(00)89059-0

文献信息

• Novel Glycosidation Method Using 2,6-Anhydro-2-thio Sugars for Stereocontrolled Synthesis of 2,6-Dideoxy-.alpha.- and -.beta.-glycosides
  作者：Kazunobu Toshima、Satsuki Mukaiyama、Yuko Nozaki、Hatsuki Inokuchi、Masaya Nakata、Kuniaki Tatsuta

  DOI：10.1021/ja00099a022

  日期：1994.10

  Powerful and highly stereocontrolled O-glycosidation methods using several kinds of 2,6-anhydro-2-thio sugars as glycosyl donors have been developed for the synthesis of both 2,6-dideoxy-alpha- and -beta-glycosides which frequently occur in biologically important natural products. Both glycosidations of phenyl 3,4-di-O-acetyl-2,6-anhydro-1,2-dithio-D-altropyranoside (2) and 3,4-di-O-acetyl-2,6-anhydro-1-fluoro-2-thio-D-altropyranoside (3) with alcohols exclusively gave the corresponding 2,6-anhydro-2-thio-alpha-glycosides. In contrast, the glycosidations of 1,3,4-tri-O-acetyl-2,6-anhydro-2-thio-D-altropyranos (4) with alcohols afforded the corresponding 2,6-anhydro-2-thio-beta-glycosides with high stereocontrol. Furthermore, a novel method for the controlled block synthesis of 2,6-dideoxy oligosaccharides by the combined use of the activated 2,6-anhydro-2-thio sugar 23 and the deactivated 2,6-anhydro-2-sulfinyl sugar 24, both of which have the same thiophenyl leaving group at the anomeric positions, has been demonstrated. The 2,6-anhydro-2-thio-alpha- and -beta-glycosides obtained by the present methods were effectively converted into the corresponding 2,6-dideoxy-alpha- and -beta-glycosides by both hydrogenolysis using Raney-Ni as a catalyst and reductive desulfurization using Bu(3)SnH and AIBN.
• TOSHIMA, KAZUNOBU;MUKAIYAMA, SATSUKI;ISHIYAMA, TAKASHI;TATSUTA, KUNIAKI, TETRAHEDRON LETT., 31,(1990) N4, C. 6361-6362
  作者：TOSHIMA, KAZUNOBU、MUKAIYAMA, SATSUKI、ISHIYAMA, TAKASHI、TATSUTA, KUNIAKI

  DOI：——

  日期：——