1,2:3,4-di-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranose
• 英文别名: tert-butyl-diphenyl-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]silane
• 化学式: C₂₈H₃₈O₆Si
• 分子量: 498.692
• InChiKey: OFYIHEYZDIHULW-ZLOLNMDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  双丙酮半乳糖 生成 1,2:3,4-di-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranose
  参考文献：
  名称：

  NASHED, EUGENIA M.;GLAUDEMANS, CORNELIS P. J., J. ORG. CHEM., 52,(1987) N 23, 5255-5260

  摘要：

  DOI：

文献信息

• Conformation of the Galactose Ring Adopted in Solution and in Crystalline Form as Determined by Experimental and DFT ¹H NMR and Single-Crystal X-ray Analysis
  作者：Mattias U. Roslund、Karel D. Klika、Reko L. Lehtilä、Petri Tähtinen、Reijo Sillanpää、Reko Leino

  DOI：10.1021/jo035400u

  日期：2004.1.1

  The solution-state conformations of various galactose derivatives were determined by comparison of the experimental H-1-H-1 vicinal coupling constants to those calculated using density functional theory (DFT) at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. The agreement between the experimental and calculated vicinal coupling constants for 1,2:3,4-di-O-isopropylidene- alpha-D-galactopyranose was good, thereby confirming an S-0(2) skew conformation for it and its derivatives on the basis of their similar observed couplings. Single-crystal X-ray analysis of 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-beta-D-glucopyranoyl)-alpha-D-galacto-pyranose and 1,2,3,4,6-penta-O-acetyl-alpha-D-galactopyranose provided S-0(2) and C-4(1), conformations, respectively, for the galactose ring in the solid state. The solid-state structures proved to be suitable starting structures for further DFT structure refinement or for immediate calculation of the coupling constants.