[(1R)-2-oxo-2-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]-1-[(2S,6S)-2-[tri(propan-2-yl)silyloxymethyl]-3,6-dihydro-2H-pyran-6-yl]ethyl] 2,2-dimethylpropanoate | 1423016-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: [(1R)-2-oxo-2-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]-1-[(2S,6S)-2-[tri(propan-2-yl)silyloxymethyl]-3,6-dihydro-2H-pyran-6-yl]ethyl] 2,2-dimethylpropanoate
• CAS: 1423016-82-3
• 化学式: C₂₈H₄₉NO₅S₂Si
• 分子量: 571.918
• InChiKey: DGXLEHOFDMBQBV-UARRHKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1R)-2-oxo-2-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]-1-[(2S,6S)-2-[tri(propan-2-yl)silyloxymethyl]-3,6-dihydro-2H-pyran-6-yl]ethyl] 2,2-dimethylpropanoate 、 lithium 1-ethoxyethenolate 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到[(1R)-4-ethoxy-2,4-dioxo-1-[(2S,6S)-2-[tri(propan-2-yl)silyloxymethyl]-3,6-dihydro-2H-pyran-6-yl]butyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosides by addition of titanium enolates from a chiral N-glycolyl thiazolidinethione to glycals

  摘要：

  The Lewis acid-mediated addition of the titanium enolate from the pivaloyl-protected (S) N-glycolyl-4-isopropyl-1,3-thiazolidine-2-thione to glycals affords the corresponding syn C-alpha-glycosides in high yields and excellent diastereomeric ratios. Further removal of the chiral auxiliary permits access to enantiomerically pure C1'-pivaloyloxy pyrans in a straightforward manner. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.028
• 作为产物：
  描述：

  [(2S,4S)-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate 、 (S)-4-isopropyl-N-(2-pivaloyloxyacetyl)-1,3-thiazolidine-2-thione 在 四氯化钛 、 N,N-二异丙基乙胺 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 5.58h， 以96%的产率得到[(1R)-2-oxo-2-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]-1-[(2S,6S)-2-[tri(propan-2-yl)silyloxymethyl]-3,6-dihydro-2H-pyran-6-yl]ethyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosides by addition of titanium enolates from a chiral N-glycolyl thiazolidinethione to glycals

  摘要：

  The Lewis acid-mediated addition of the titanium enolate from the pivaloyl-protected (S) N-glycolyl-4-isopropyl-1,3-thiazolidine-2-thione to glycals affords the corresponding syn C-alpha-glycosides in high yields and excellent diastereomeric ratios. Further removal of the chiral auxiliary permits access to enantiomerically pure C1'-pivaloyloxy pyrans in a straightforward manner. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.028

文献信息

• Stereoselective synthesis of C-glycosides by addition of titanium enolates from a chiral N-glycolyl thiazolidinethione to glycals
  作者：Erik Gálvez、Miriam Sau、Pedro Romea、Fèlix Urpí、Mercè Font-Bardia

  DOI：10.1016/j.tetlet.2013.01.028

  日期：2013.3

  The Lewis acid-mediated addition of the titanium enolate from the pivaloyl-protected (S) N-glycolyl-4-isopropyl-1,3-thiazolidine-2-thione to glycals affords the corresponding syn C-alpha-glycosides in high yields and excellent diastereomeric ratios. Further removal of the chiral auxiliary permits access to enantiomerically pure C1'-pivaloyloxy pyrans in a straightforward manner. (C) 2013 Elsevier Ltd. All rights reserved.