(2R,3S,4S,6R)-6-(cyclohexyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol | 67279-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,6R)-6-(cyclohexyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol
• 英文别名: (2R,3S,4S,6R)-6-cyclohexyloxy-2-methyloxane-3,4-diol
• CAS: 67279-14-5
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: KVVFKXLEDOKWOZ-NUGNTBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,6R)-6-(cyclohexyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol 在 (S,S)-DACH-phenyl Trost ligand 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四氧化锇 、 Hoveyda-Grubbs catalyst second generation 、 [RuHCl(CO)(H₂IMes)(PCy₃)] 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 (1R,2R)-(+)-1,2-二氨基环己烷-N,N′-双(2-二苯基磷苯甲酰) 、 三甲胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 58.0h， 生成 (2R,3R,4S,6R)-3-(((2S,4S,5R,6R)-4-acetoxy-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-(cyclohexyloxy)-2-methyltetrahydro-2H-pyran-4-yl acetate
  参考文献：
  名称：

  钌催化的二氢吡喃乙缩醛的区域选择性烯烃迁移：从头开始向β-2,6-Dideoxypyranoglycosides的策略。

  摘要：

  在这里，我们报道了针对β-2,6-dideoxypyranoglycosides的从头合成策略。关键事件是二氢吡喃烯丙基乙缩醛向均烯丙基缩醛的钌催化的区域选择性烯烃迁移。结合其他金属催化的反应，该新方案导致以高效方式合成β-2,6-二脱氧吡喃葡萄糖苷。使用这种顺序的金属催化，制备了β-2，6-二脱氧吡喃葡萄糖苷的各种单糖，二糖和三糖形式。

  DOI：

  10.1021/acs.orglett.0c00279
• 作为产物：
  描述：

  (1S,3R,4S,7S,8R)-3-Cyclohexyloxy-2-oxa-5-thia-bicyclo[2.2.2]octane-7,8-diol 在 Raney-Ni (W₄) 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到(2R,3S,4S,6R)-6-(cyclohexyloxy)-2-methyltetrahydro-2H-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

文献信息

• Novel C-3 Epimerization of Digitoxosides to Olivosides Under Hydrogenolysis Conditions
  作者：Kazunobu Toshima、Kyoko Inagaki、Masaya Nakata、Shuichi Matsumura

  DOI：10.1055/s-1997-3269

  日期：1997.6

  The treatment of several β-digitoxosides with hydrogen in the presence of a catalytic amount of Raney-Ni (W4) in MeOH at 50 °C under neutral conditions afforded the C-3 epimers, β-olivosides, in good yields.

  在中性条件下，于 50 °C 的 MeOH 溶液中，在一定量的 Raney-Ni (W4) 催化剂存在下，用氢气处理几种 δ-二甲氧基苷，可以得到 C-3 外延物--δ-寡糖苷，收率很高。