(2S,3S)-3-Amino-3-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol | 146467-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S,3S)-3-Amino-3-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol
• 英文别名: (2S,3S)-3-amino-3-[(4R,5R)-2,2-dimethyl-5-(trityloxymethyl)-1,3-dioxolan-4-yl]propane-1,2-diol
• CAS: 146467-10-9
• 化学式: C₂₈H₃₃NO₅
• 分子量: 463.574
• InChiKey: ONIKHGQOIIACCG-XPGKHFPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Amino-3-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol 在 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 生成 (R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid
  参考文献：
  名称：

  Studies on lactams. 89. Versatile .beta.-lactam synthons: enantiospecific synthesis of (-)-polyoxamic acid

  摘要：

  An optically pure cis-alpha-hydroxy beta-lactam of predictable absolute configuration prepared from readily available D-mannitol has been utilized for the synthesis of the non-natural enantiomer of polyoxamic acid through a series of stereospecific reactions.

  DOI：

  10.1021/jo00054a007
• 作为产物：
  描述：

  cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 甲酸铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (2S,3S)-3-Amino-3-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol
  参考文献：
  名称：

  Studies on lactams. 89. Versatile .beta.-lactam synthons: enantiospecific synthesis of (-)-polyoxamic acid

  摘要：

  An optically pure cis-alpha-hydroxy beta-lactam of predictable absolute configuration prepared from readily available D-mannitol has been utilized for the synthesis of the non-natural enantiomer of polyoxamic acid through a series of stereospecific reactions.

  DOI：

  10.1021/jo00054a007

文献信息

• Studies on lactams. 89. Versatile .beta.-lactam synthons: enantiospecific synthesis of (-)-polyoxamic acid
  作者：Bimal K. Banik、Maghar S. Manhas、Ajay K. Bose

  DOI：10.1021/jo00054a007

  日期：1993.1

  An optically pure cis-alpha-hydroxy beta-lactam of predictable absolute configuration prepared from readily available D-mannitol has been utilized for the synthesis of the non-natural enantiomer of polyoxamic acid through a series of stereospecific reactions.
• Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques
  作者：Ajay K Bose、Bimal K Banik、Chandra Mathur、Dilip R Wagle、Maghar S Manhas

  DOI：10.1016/s0040-4020(00)00410-5

  日期：2000.7

  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.