tert-butyl β-D-digitoxoside | 117399-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl β-D-digitoxoside
• 英文别名: (2R,3S,4S,6S)-2-methyl-6-[(2-methylpropan-2-yl)oxy]oxane-3,4-diol
• CAS: 117399-46-9
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: NQMSROAYHNIBJS-RYPBNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  tert-butyl β-D-digitoxoside 生成 1-thioethyl-3,4-di-O-benzoyl-α-D-digitoxide
  参考文献：
  名称：

  BINKLEY, ROGER W.;SCHNEIDER, J. STEVEN, J. CARBOHYDR. CHEM., 7,(1988) N 1, 157-167

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3,4-di-O-acetyl-2,6-anhydro-2-thio-D-α-altropyranoside 在 Raney-Ni (W₄) 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 sodium methylate 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 tert-butyl 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

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。