(+)-(3S,4S,5S)-1-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxymethyl-4-(2-furyl)-5-trimethylsilylpyrazolidine | 224572-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (+)-(3S,4S,5S)-1-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxymethyl-4-(2-furyl)-5-trimethylsilylpyrazolidine
• 英文别名: tert-butyl (3S,4S,5S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(furan-2-yl)-5-trimethylsilylpyrazolidine-1-carboxylate
• CAS: 224572-06-9
• 化学式: C₂₂H₄₂N₂O₄Si₂
• 分子量: 454.757
• InChiKey: AJKOVZPUHIUNHQ-NEWSRXKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  63.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4S,5S)-1-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxymethyl-4-(2-furyl)-5-trimethylsilylpyrazolidine 在 jones reagent 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 生成 (+)-3-<(3S,4S,5S)-2-benzyloxycarbonyl-1-(tert-butoxycarbonyl)-4-(2-furyl)-5-trimethylsilylpyrazolidine>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：

  (+)-(1R,2S,5R)-8-phenylmenthyl 3-((4S,5S)-1-tert-butoxycarbonyl-4-(2-furyl)-4,5-dihydro-5-trimethylsilyl-1H-pyrazole)carboxylate 在 咪唑 、 sodium tetrahydroborate 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (+)-(3S,4S,5S)-1-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxymethyl-4-(2-furyl)-5-trimethylsilylpyrazolidine
  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