1,3,4,5-tetrakis(tert-butyldimethylsilyloxy)-6-tert-butyldimethylsilyloxymethyl-(3R,4S,5R,6S)-tetrahydropyridin-2(1H)-one | 911380-62-6

• 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: 1,3,4,5-tetrakis(tert-butyldimethylsilyloxy)-6-tert-butyldimethylsilyloxymethyl-(3R,4S,5R,6S)-tetrahydropyridin-2(1H)-one
• 英文别名: (3R,4S,5R,6S)-1,3,4,5-tetrakis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]piperidin-2-one
• CAS: 911380-62-6
• 化学式: C₃₆H₈₁NO₆Si₅
• 分子量: 764.47
• InChiKey: BWXMMICTXFLYNT-RRGQHJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.33
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetrakis(tert-butyldimethylsilyloxy)-6-tert-butyldimethylsilyloxymethyl-(3R,4S,5R,6S)-tetrahydropyridin-2(1H)-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以76%的产率得到3,4,5-tris(tert-butyldimethylsilyloxy)-6-tert-butyldimethylsilyloxymethyl-(3R,4S,5R,6S)-2-piperidinone
  参考文献：
  名称：

  Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars

  摘要：

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.

  DOI：

  10.1002/chem.200600268
• 作为产物：
  描述：

  (2R,3S,4R,5R)-N,2,3,4,6-pentakis[[tert-butyl(dimethyl)silyl]oxy]-5-hydroxyhexanamide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 以81%的产率得到1,3,4,5-tetrakis(tert-butyldimethylsilyloxy)-6-tert-butyldimethylsilyloxymethyl-(3R,4S,5R,6S)-tetrahydropyridin-2(1H)-one
  参考文献：
  名称：

  Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars

  摘要：

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.

  DOI：

  10.1002/chem.200600268