((2S,3S)-6-Hydroxy-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester | 914799-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2S,3S)-6-Hydroxy-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester
• CAS: 914799-37-4
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: ISUJZZLCCBCBRY-JVIMKECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-6-Hydroxy-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester 在 吡啶 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 cyclopentyl 2,3,4,6-tetradeoxy-4-(tert-butoxycarbonylamino)-threo-hexose
  参考文献：
  名称：

  Synthetic Studies ofN‐demethylossamine and Elaboration of its Glycosylation

  摘要：

  An amino-sugar, N -demethylossamine, was efficiently synthesized from D-threonine, two stereogenic centers of which were directly used as those at the C-4 and 5 positions of the target sugar. In addition, the glycosylation study indicated that reaction of the acetate 7 with cyclopentanol under Lewis acid conditions, provided the desired alpha-L-glycoside 9 alpha.

  DOI：

  10.1080/07328300600778793
• 作为产物：
  描述：

  (5S,6S)-3,4,5,6-tetrahydro-5-(tert-butoxycarbonylamino)-6-methyl-2-pyrone 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以100%的产率得到((2S,3S)-6-Hydroxy-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthetic Studies ofN‐demethylossamine and Elaboration of its Glycosylation

  摘要：

  An amino-sugar, N -demethylossamine, was efficiently synthesized from D-threonine, two stereogenic centers of which were directly used as those at the C-4 and 5 positions of the target sugar. In addition, the glycosylation study indicated that reaction of the acetate 7 with cyclopentanol under Lewis acid conditions, provided the desired alpha-L-glycoside 9 alpha.

  DOI：

  10.1080/07328300600778793