[(2R,3R,4S,6R)-3-acetyloxy-6-(cyclohexylmethoxy)-2-methyloxan-4-yl] acetate | 139190-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,6R)-3-acetyloxy-6-(cyclohexylmethoxy)-2-methyloxan-4-yl] acetate
• CAS: 139190-84-4
• 化学式: C₁₇H₂₈O₆
• 分子量: 328.406
• InChiKey: WYNPGOXSPJPLNG-GLZXHMCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• 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：
  6.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,6R)-3-acetyloxy-6-(cyclohexylmethoxy)-2-methyloxan-4-yl] acetate 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以95%的产率得到(2R,3S,4S,6R)-6-Cyclohexylmethoxy-2-methyl-tetrahydro-pyran-3,4-diol
  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-dideoxy-α-D-ribo-hexopyranoside 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 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 [(2R,3R,4S,6R)-3-acetyloxy-6-(cyclohexylmethoxy)-2-methyloxan-4-yl] acetate
  参考文献：
  名称：

  通过糖基供体的构象辅助实现高度立体选择性的糖基化

  摘要：

  通过使用刚性糖基供体2的构象辅助，实现了2-脱氧-D-岩藻糖的高度α-立体选择性糖基化。2的糖基化的选择性比具有正常椅子构象的3的糖基化的选择性高得多。

  DOI：

  10.1016/0040-4039(91)80435-9

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.