(-)-(3R,4S)-2-benzyloxycarbonyl-1-(tert-butoxycarbonyl)-3-tert-butyldimethylsilyloxymethyl-4-phenylpyrazolidine | 224572-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: (-)-(3R,4S)-2-benzyloxycarbonyl-1-(tert-butoxycarbonyl)-3-tert-butyldimethylsilyloxymethyl-4-phenylpyrazolidine
• CAS: 224572-15-0
• 化学式: C₂₉H₄₂N₂O₅Si
• 分子量: 526.748
• InChiKey: KZHPLQWWMOZXSX-RPBOFIJWSA-N

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4S)-2-benzyloxycarbonyl-1-(tert-butoxycarbonyl)-3-tert-butyldimethylsilyloxymethyl-4-phenylpyrazolidine 在 jones reagent 作用下， 以97%的产率得到(-)-<(3R,4S)-2-benzyloxycarbonyl-1-(tert-butoxycarbonyl)-4-phenylpyrazolidine>carboxylic acid
  参考文献：
  名称：

  First Highly Regio- and Diastereoselective [3+2] Cycloaddition of Chiral Nonracemic Alkenyl Fischer Carbene Complexes with Diazomethane Derivatives: Preparation and Synthetic Applications of Enantiomerically Pure Δ2-Pyrazolines

  摘要：

  The [3+2] cycloaddition of alkenyl Fischer carbene complexes 1 and 6 with diazomethane derivatives to give Delta(2)-pyrazoline carbenes 2, 4, and 7 is described. The conversion of (-)-8-phenylmenthol-derived carbenes 6 into pyrazoline esters 9 through a one-pot cycloaddition-protection-oxidation is presented as an expeditious route to enantiomerically pure 3-alkoxycarbon-yl-Delta(2)-pyrazolines in good yields and in a highly regio- and diastereoselective manner. Pyrazolidines 13 were synthesized in excellent overall yields from 9 through pyrazolines 11 and 12, the diastereoselective reduction of C=N bond being the key step. Azaprolines 16 and 17 were prepared in very good yields from epimeric trans-13 or cis-13 by oxidative deprotection of the silylated hydroxy group. In an alternative reaction, the pyrazolidine ring of 13 was reduced to obtain protected open-chain 2,4-diamino alcohols 19 with three chiral centers.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<883::aid-chem883>3.0.co;2-0
• 作为产物：
  描述：

  (-)-(4S)-1-tert-butoxycarbonyl-4,5-dihydro-3-hydroxymethyl-4-phenyl-1H-pyrazole 在 咪唑 、 三乙基硼氢化锂 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 (-)-(3R,4S)-2-benzyloxycarbonyl-1-(tert-butoxycarbonyl)-3-tert-butyldimethylsilyloxymethyl-4-phenylpyrazolidine
  参考文献：
  名称：

  First Highly Regio- and Diastereoselective [3+2] Cycloaddition of Chiral Nonracemic Alkenyl Fischer Carbene Complexes with Diazomethane Derivatives: Preparation and Synthetic Applications of Enantiomerically Pure Δ2-Pyrazolines

  摘要：

  The [3+2] cycloaddition of alkenyl Fischer carbene complexes 1 and 6 with diazomethane derivatives to give Delta(2)-pyrazoline carbenes 2, 4, and 7 is described. The conversion of (-)-8-phenylmenthol-derived carbenes 6 into pyrazoline esters 9 through a one-pot cycloaddition-protection-oxidation is presented as an expeditious route to enantiomerically pure 3-alkoxycarbon-yl-Delta(2)-pyrazolines in good yields and in a highly regio- and diastereoselective manner. Pyrazolidines 13 were synthesized in excellent overall yields from 9 through pyrazolines 11 and 12, the diastereoselective reduction of C=N bond being the key step. Azaprolines 16 and 17 were prepared in very good yields from epimeric trans-13 or cis-13 by oxidative deprotection of the silylated hydroxy group. In an alternative reaction, the pyrazolidine ring of 13 was reduced to obtain protected open-chain 2,4-diamino alcohols 19 with three chiral centers.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<883::aid-chem883>3.0.co;2-0