n-octyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-α-D-altropyranoside | 130427-30-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-octyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-α-D-altropyranoside
• CAS: 130427-30-4
• 化学式: C₁₈H₃₀O₆S
• 分子量: 374.499
• InChiKey: VXPNMQQFDWENNC-DZVNLGKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  n-octyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-α-D-altropyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.5h， 生成 n-octyl 2,6-dideoxy-α-D-ribo-hexopyranoside
  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：

  methyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-D-α-altropyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.75h， 生成 n-octyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-α-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

• 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.