(S)-4-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester | 852609-51-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-4-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 852609-51-9
• 化学式: C₂₇H₃₉NO₄Si
• 分子量: 469.696
• InChiKey: QYSNUSCMDVXJAB-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 bismuth(III) bromide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以92%的产率得到tert-butyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate
  参考文献：
  名称：

  Chemoselective Deprotection of Cyclic N,O-Aminals Using Catalytic Bismuth(III) Bromide in Acetonitrile

  摘要：

  Cyclic N,O-aminals can be chemoselectively and efficiently deprotected using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This selectivity was also achieved in the presence of terminal O,O-acetal functionality. The susceptibility of various other groups to cleavage was also investigated. This method has advantages of ease of operation and use of nontoxic and inexpensive reagents in catalytic amounts.

  DOI：

  10.1021/jo050228a
• 作为产物：
  描述：

  (R)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(S)-4-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis

  摘要：

  Three new diastereomeric shikimic acid analogues (4-amino-3,5-dihydroxyl-cyclohex-1-en-carboxylic acids, 16) bearing a C-4 amino group were synthesized in parallel by a mixture-operation protocol. Ring-closing enyne metathesis (RCEYM) under ethylene atmosphere was successfully employed to construct the desired carbocycles in high efficiency. The absolute configurations of each final product were confirmed by the ID and 2D NMR techniques. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.118

文献信息

• Chemoselective Deprotection of Cyclic <i>N</i>,<i>O</i>-Aminals Using Catalytic Bismuth(III) Bromide in Acetonitrile
  作者：Xin Cong、Fang Hu、Ke-Gang Liu、Qing-Jiang Liao、Zhu-Jun Yao

  DOI：10.1021/jo050228a

  日期：2005.5.1

  Cyclic N,O-aminals can be chemoselectively and efficiently deprotected using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This selectivity was also achieved in the presence of terminal O,O-acetal functionality. The susceptibility of various other groups to cleavage was also investigated. This method has advantages of ease of operation and use of nontoxic and inexpensive reagents in catalytic amounts.
• Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis
  作者：Fang Hu、Yan-Hong Zhang、Zhu-Jun Yao

  DOI：10.1016/j.tetlet.2007.03.118

  日期：2007.5

  Three new diastereomeric shikimic acid analogues (4-amino-3,5-dihydroxyl-cyclohex-1-en-carboxylic acids, 16) bearing a C-4 amino group were synthesized in parallel by a mixture-operation protocol. Ring-closing enyne metathesis (RCEYM) under ethylene atmosphere was successfully employed to construct the desired carbocycles in high efficiency. The absolute configurations of each final product were confirmed by the ID and 2D NMR techniques. (C) 2007 Elsevier Ltd. All rights reserved.