2,4-dimethyl-3-pentyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside | 131922-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2,4-dimethyl-3-pentyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside
• 英文别名: [(1S,3R,4S,7R,8R)-8-acetyloxy-3-(2,4-dimethylpentan-3-yloxy)-2-oxa-5-thiabicyclo[2.2.2]octan-7-yl] acetate
• CAS: 131922-40-2
• 化学式: C₁₇H₂₈O₆S
• 分子量: 360.472
• InChiKey: WUGYLEZAYILOIC-MNLARUNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-3-pentyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside 在 Raney-Ni (W₄) 甲醇 、 氢气 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (2,4-dimethyl-3-pentyl) β-D-digitoxoside
  参考文献：
  名称：

  Novel Glycosidation Method Using 2,6-Anhydro-2-thio Sugars for Stereocontrolled Synthesis of 2,6-Dideoxy-.alpha.- and -.beta.-glycosides

  摘要：

  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.

  DOI：

  10.1021/ja00099a022
• 作为产物：
  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 2.5h， 生成 2,4-dimethyl-3-pentyl 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

文献信息

• The use of 2,6-anhydro-2-thio sugar for a highly stereocontrolled glycosylation: A novel strategy for synthesis of 2,6-dideoxy-α-glycosides
  作者：Kazunobu Toshima、Satsuki Mukaiyama、Takashi Ishiyama、Kuniaki Tatsuta

  DOI：10.1016/s0040-4039(00)89059-0

  日期：——

  A novel and efficient synthesis of 2,6-dideoxy-α-glycosides was developed by use of phenyl 2,6-anhydro-1,2-dithio-D-altropyranosides as glycosyl donors in a highly stereocontrolled glycosylation.

  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。
• Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides
  作者：Kazunobu Toshima、Yuko Nozaki、Satsuki Mukaiyama、Kuniaki Tatsuta

  DOI：10.1016/s0040-4039(00)91656-3

  日期：1992.3

  Gycosylations of the 1-O-acetyl-2,6-anhydro-2-thio sugar 3 with alcohols in the presence of several Lewis acids in CH2Cl2 proceeded smoothly to give the corresponding beta-O-glycosides with high stereocontrol in high yields, and the selectivity of the glycosylation was highly independent on Lewis acids.
• 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：——