[(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl]-carbamic acid tert-butyl ester | 301532-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl]-carbamic acid tert-butyl ester
• CAS: 301532-95-6
• 化学式: C₁₃H₂₅NO₆
• 分子量: 291.345
• InChiKey: XDJLABCAGFVURE-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  97.25
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl]-carbamic acid tert-butyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以80%的产率得到(S)-tert-Butoxycarbonylamino-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid
  参考文献：
  名称：

  Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques

  摘要：

  Enantiospecific synthesis has been developed for alpha-hydroxy beta-lactams of predictable absolute configuration starting with readily available carbohydrates, Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epilincosamine, gamma-hydroxythreonine, and polyoxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00410-5
• 作为产物：
  描述：

  (+)-(3R,4S)-cis-1-benzyl-3-benzyloxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone 在 palladium on activated charcoal sodium hydroxide 、 lithium aluminium tetrahydride 、 ammonium formate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.1h， 生成 [(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques

  摘要：

  Enantiospecific synthesis has been developed for alpha-hydroxy beta-lactams of predictable absolute configuration starting with readily available carbohydrates, Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epilincosamine, gamma-hydroxythreonine, and polyoxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00410-5