methyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)sulfonyloxybutanoate | 395063-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)sulfonyloxybutanoate
• CAS: 395063-34-0
• 化学式: C₂₇H₂₇NO₇S
• 分子量: 509.58
• InChiKey: UMNPGCLJMNDHDS-CJAUYULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)sulfonyloxybutanoate 、 potassium thioacyanate 以 乙腈 为溶剂， 反应 15.0h， 以65%的产率得到methyl (2R,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-thiocyanatobutanoate
  参考文献：
  名称：

  Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form

  摘要：

  A simple and efficient method for the synthesis of allo- and threo-3,3'-dimethylcystine derivatives is reported. Various tosyl and bromo derivatives of Cbz-, Boc-, and Fmoc- Protected threonine rnethyl esters have been prepared and subjected to nucleophilic substitution with potassium thiocyanate in acetonitrile to yield the corresponding thiocyanate derivatives in moderate yield. The thiocyanates are readily converted to the corresponding allo- and threo-3,3'-dimethylcystine derivatives via reductive dimerization with benzyltriethylammonium tetrathiomolybdate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.001
• 作为产物：
  描述：

  Fmoc-Thr-OMe 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 60.0h， 以77%的产率得到methyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)sulfonyloxybutanoate
  参考文献：
  名称：

  Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form

  摘要：

  A simple and efficient method for the synthesis of allo- and threo-3,3'-dimethylcystine derivatives is reported. Various tosyl and bromo derivatives of Cbz-, Boc-, and Fmoc- Protected threonine rnethyl esters have been prepared and subjected to nucleophilic substitution with potassium thiocyanate in acetonitrile to yield the corresponding thiocyanate derivatives in moderate yield. The thiocyanates are readily converted to the corresponding allo- and threo-3,3'-dimethylcystine derivatives via reductive dimerization with benzyltriethylammonium tetrathiomolybdate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.001

文献信息

• Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form
  作者：R.B. Nasir Baig、V. Sai Sudhir、Srinivasan Chandrasekaran

  DOI：10.1016/j.tetasy.2008.06.001

  日期：2008.6

  A simple and efficient method for the synthesis of allo- and threo-3,3'-dimethylcystine derivatives is reported. Various tosyl and bromo derivatives of Cbz-, Boc-, and Fmoc- Protected threonine rnethyl esters have been prepared and subjected to nucleophilic substitution with potassium thiocyanate in acetonitrile to yield the corresponding thiocyanate derivatives in moderate yield. The thiocyanates are readily converted to the corresponding allo- and threo-3,3'-dimethylcystine derivatives via reductive dimerization with benzyltriethylammonium tetrathiomolybdate. (C) 2008 Elsevier Ltd. All rights reserved.