tert-butyl N-[(3aS,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-4-methylidene-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]carbamate | 247191-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[(3aS,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-4-methylidene-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]carbamate
• CAS: 247191-07-7
• 化学式: C₁₄H₂₃NO₅
• 分子量: 285.34
• InChiKey: PJNHSMBEGNNRIU-VPOLOUISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(3aS,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-4-methylidene-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]carbamate 在 盐酸 、 硼烷四氢呋喃络合物 作用下， 反应 12.0h， 生成 (1S,2S,3S,4R,5R)-4-amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol hydrochloride
  参考文献：
  名称：

  Anomer-Selective Inhibition of Glycosidases Using Aminocyclopentanols

  摘要：

  [GRAPHICS](1S,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1 is prepared stereoselectively from D-lyxose and displays anomer selective inhibition for beta galactosidase (K-i = 3.0 x 10(-6) M) and beta-glucosidase (K-i = 1.5 x 10(-7) M), over alpha-galactosidase (K-i = 2.3 x 10(-5) M) and a glucosidase (IC50 = 1.0 x 10(-4) M), There is no observable cross-reactivity with alpha-mannosidase, beta-mannosidase, or alpha-L-fucosidase.

  DOI：

  10.1021/ol990754m
• 作为产物：
  描述：

  (2S,3S,4S,5R)-1-methylene-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentane 在 ammonium hydroxide 、 碳酸氢钠 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 tert-butyl N-[(3aS,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-4-methylidene-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]carbamate
  参考文献：
  名称：

  Anomer-Selective Inhibition of Glycosidases Using Aminocyclopentanols

  摘要：

  [GRAPHICS](1S,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1 is prepared stereoselectively from D-lyxose and displays anomer selective inhibition for beta galactosidase (K-i = 3.0 x 10(-6) M) and beta-glucosidase (K-i = 1.5 x 10(-7) M), over alpha-galactosidase (K-i = 2.3 x 10(-5) M) and a glucosidase (IC50 = 1.0 x 10(-4) M), There is no observable cross-reactivity with alpha-mannosidase, beta-mannosidase, or alpha-L-fucosidase.

  DOI：

  10.1021/ol990754m