(1S,2R,3R,4S,5R)-2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester | 445469-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,2R,3R,4S,5R)-2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester
• CAS: 445469-31-8
• 化学式: C₃₀H₆₁NO₆Si₃
• 分子量: 616.074
• InChiKey: GQEUOUDBWLXNPF-VCDBXAJLSA-N

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4S,5R)-2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到(1S,2R,3R,4S,5R)-5-tert-butoxycarbonylamino-2,4-bis-(tert-butyldimethyl-silanyloxy)-3-(triethylsilanyloxy)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 4.¹ Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof

  摘要：

  A chiral, divergent synthesis of two carbafuranosylamines, I and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.

  DOI：

  10.1021/jo0257905
• 作为产物：
  描述：

  (1S,3R,4S,5R)-6-Benzyl-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-6-aza-bicyclo[3.2.1]octan-7-one 在 4-二甲氨基吡啶 、 sodium 作用下， 以 四氢呋喃 、 氨 、 乙腈 为溶剂， 反应 4.5h， 生成 (1S,2R,3R,4S,5R)-2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 4.¹ Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof

  摘要：

  A chiral, divergent synthesis of two carbafuranosylamines, I and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.

  DOI：

  10.1021/jo0257905