n-octyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside | 141299-50-5

• 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-β-D-altropyranoside
• CAS: 141299-50-5
• 化学式: C₁₈H₃₀O₆S
• 分子量: 374.499
• InChiKey: VXPNMQQFDWENNC-HSFUPAIVSA-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-β-D-altropyranoside 在 甲醇 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 n-octyl 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：

  methyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-D-α-altropyranoside 在 三氟甲磺酸三甲基硅酯 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 n-octyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-β-D-altropyranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)91656-3