2-acetamido-2-deoxy-D-xylono-1,4-lactone | 117771-09-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-2-deoxy-D-xylono-1,4-lactone
• 英文别名: N-[(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-oxooxolan-3-yl]acetamide
• CAS: 117771-09-2
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: SFSOCLFOPIFBBR-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-5-benzyloxy-4-bromo-1-(4-methylphenylsulfinyl)pentane-2,3-diol 在 palladium dihydroxide 咪唑 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium azide 、 碘苯二乙酸 、 camphor-10-sulfonic acid 、 氢气 、 三乙胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 48.58h， 生成 2-acetamido-2-deoxy-D-xylono-1,4-lactone
  参考文献：
  名称：

  The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

  摘要：

  A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio- and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01650-2

文献信息

• 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.
• Bols, Mikael; Lundt, Inge, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 67 - 74
  作者：Bols, Mikael、Lundt, Inge

  DOI：——

  日期：——
• 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.
• BOLS, MIKAEL;LUNDT, INGE, ACTA CHEM. SCAND., 42,(1988) N 2, 67-74
  作者：BOLS, MIKAEL、LUNDT, INGE

  DOI：——

  日期：——