(S)-4-((S)-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl-d)-1,3-dioxolane-2-thione | 136089-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-((S)-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl-d)-1,3-dioxolane-2-thione
• 英文别名: 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate
• CAS: 136089-06-0
• 化学式: C₃₈H₄₀O₇S
• 分子量: 641.789
• InChiKey: INKQDXTZMSMPCQ-UUBSQZAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-4-((S)-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl-d)-1,3-dioxolane-2-thione 在 palladium dihydroxide 氢气 、 三甲氧基磷 作用下， 以 甲醇 为溶剂， 反应 67.0h， 生成 1-(α-D-glucopyranosyl)-1(R)-deuteriopropane
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 6. Conformational similarity of glycosides and corresponding C-glycosides

  摘要：

  The conformation of the alpha-(axial)-C-glycosides 1-3 and the beta-(equatorial)-C-glycosides 4-6 were studied by H-1 NMR. Their preferred solution conformation was found to match that of the corresponding parent glycosides. The study of 2-deoxy compounds 13-16 shows that the preference is due primarily to gauche interactions around the glycosidic bond. Solvent studies indicate that electrostatic interactions and hydrogen bonds do not significantly alter the overall conformation. Temperature studies suggest that these compounds exist as an equilibrium mixture of conformers.

  DOI：

  10.1021/jo00022a038
• 作为产物：
  描述：

  methyl 3-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)propenoate 在 sodium hydroxide 、 双氧水 、 borane-d3 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 20.5h， 生成 (S)-4-((S)-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl-d)-1,3-dioxolane-2-thione
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 6. Conformational similarity of glycosides and corresponding C-glycosides

  摘要：

  The conformation of the alpha-(axial)-C-glycosides 1-3 and the beta-(equatorial)-C-glycosides 4-6 were studied by H-1 NMR. Their preferred solution conformation was found to match that of the corresponding parent glycosides. The study of 2-deoxy compounds 13-16 shows that the preference is due primarily to gauche interactions around the glycosidic bond. Solvent studies indicate that electrostatic interactions and hydrogen bonds do not significantly alter the overall conformation. Temperature studies suggest that these compounds exist as an equilibrium mixture of conformers.

  DOI：

  10.1021/jo00022a038

文献信息

• Preferred conformation of C-glycosides. 7. Preferred conformation of carbon analogs of isomaltose and gentiobiose
  作者：Peter G. Goekjian、Tse Chong Wu、Han Young Kang、Yoshito Kishi

  DOI：10.1021/jo00022a039

  日期：1991.10

  The preferred solution conformation of the 1,6-linked C-disaccharides 3 and 4, carbon analogues of methyl isomaltoside and methyl gentiobioside, was shown to be 3-A and 4-A, respectively, by H-1 NMR spectroscopy.