(S)-N-[(2R,3R)-3-benzyloxy-2-pivaloyloxy-5-triisopropylsilyloxypentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione | 1400585-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-[(2R,3R)-3-benzyloxy-2-pivaloyloxy-5-triisopropylsilyloxypentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione
• 英文别名: [(2R,3R)-1-oxo-3-phenylmethoxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]-5-tri(propan-2-yl)silyloxypentan-2-yl] 2,2-dimethylpropanoate
• CAS: 1400585-86-5
• 化学式: C₃₂H₅₃NO₅S₂Si
• 分子量: 623.994
• InChiKey: OEFBFDFBROQCKE-JCYYIGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  (S)-N-[(2R,3R)-3-benzyloxy-2-pivaloyloxy-5-triisopropylsilyloxypentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione 、 二甲羟胺盐酸盐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以84%的产率得到(2R,3R)-3-benzyloxy-N-methoxy-N-methyl-2-pivaloyloxy-5-triisopropylsilyloxypentanamide
  参考文献：
  名称：

  Diastereoselective Additions of Titanium Enolates from N-Glycolyl Thiazolidinethiones to Acetals

  摘要：

  The stereochemical outcome of the Lewis acid-mediated glycolate addition of the titanium enolates from protected N-hydroxyacetyl-4-isopropyl-1,3-thiazolidine-2-thiones to dimethyl and dibenzyl acetals depends on the hydroxyl protecting group. Particularly, the pivaloyl protected glycolate derivative provides the reluctant anti adducts in high yields and diastereomeric ratios, which can be isolated and further converted in enantiomerically pure form to beta-methoxy or beta-benzyloxy alpha-pivaloyloxy carbonyl fragments in a straightforward manner.

  DOI：

  10.1021/jo301569x
• 作为产物：
  描述：

  三甲基乙酰氯 在 4-二甲氨基吡啶 、 四氯化钛 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 57.33h， 生成 (S)-N-[(2R,3R)-3-benzyloxy-2-pivaloyloxy-5-triisopropylsilyloxypentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione 、 (S)-N-[(2R,3S)-3-benzyloxy-2-pivaloyloxy-5-triisopropylsilyloxypentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Diastereoselective Additions of Titanium Enolates from N-Glycolyl Thiazolidinethiones to Acetals

  摘要：

  The stereochemical outcome of the Lewis acid-mediated glycolate addition of the titanium enolates from protected N-hydroxyacetyl-4-isopropyl-1,3-thiazolidine-2-thiones to dimethyl and dibenzyl acetals depends on the hydroxyl protecting group. Particularly, the pivaloyl protected glycolate derivative provides the reluctant anti adducts in high yields and diastereomeric ratios, which can be isolated and further converted in enantiomerically pure form to beta-methoxy or beta-benzyloxy alpha-pivaloyloxy carbonyl fragments in a straightforward manner.

  DOI：

  10.1021/jo301569x

文献信息

• Diastereoselective Additions of Titanium Enolates from <i>N</i>-Glycolyl Thiazolidinethiones to Acetals
  作者：Jessica Baiget、Marta Caba、Erik Gálvez、Pedro Romea、Fèlix Urpí、Mercè Font-Bardia

  DOI：10.1021/jo301569x

  日期：2012.10.5

  The stereochemical outcome of the Lewis acid-mediated glycolate addition of the titanium enolates from protected N-hydroxyacetyl-4-isopropyl-1,3-thiazolidine-2-thiones to dimethyl and dibenzyl acetals depends on the hydroxyl protecting group. Particularly, the pivaloyl protected glycolate derivative provides the reluctant anti adducts in high yields and diastereomeric ratios, which can be isolated and further converted in enantiomerically pure form to beta-methoxy or beta-benzyloxy alpha-pivaloyloxy carbonyl fragments in a straightforward manner.