3-Amino-3-deoxy-α-D-mannose | 802048-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Amino-3-deoxy-α-D-mannose
• 英文别名: 3-Amino-3-desoxy-α-D-mannose；3-Amino-3-desoxy-α-D-mannopyranose；(2S,3S,4S,5S,6R)-4-amino-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 802048-19-7
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: BQCCAEOLPYCBAE-RDQKPOQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Amino-3-deoxy-α-D-mannose 、 乙酸酐 在 silver(I) acetate 作用下， 以 甲醇 为溶剂， 生成 3-Acetamido-3-desoxy-β-D-mannose
  参考文献：
  名称：

  Cyclizations of Dialdehydes with Nitromethane. III.¹ Preparation of 3-Amino-3-deoxy-D-mannose

  摘要：

  DOI：

  10.1021/ja01499a060
• 作为产物：
  描述：

  methyl 3-amino-3-deoxy-α-D-mannopyranoside 在 盐酸 作用下， 生成 3-Amino-3-deoxy-α-D-mannose
  参考文献：
  名称：

  Cyclizations of Dialdehydes with Nitromethane. III.¹ Preparation of 3-Amino-3-deoxy-D-mannose

  摘要：

  DOI：

  10.1021/ja01499a060

文献信息

• Aldotetroses and C(3)-Modified Aldohexoses as Substrates for N-Acetylneuraminic Acid Aldolase: A Model for the Explanation of the Normal and the Inversed Stereoselectivity
  作者：Wolfgang Fitz、Jan-Robert Schwark、Chi-Huey Wong

  DOI：10.1021/jo00117a016

  日期：1995.6

  The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase. C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition. Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions. The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.
• Cyclizations of Dialdehydes with Nitromethane. III.¹ Preparation of 3-Amino-3-deoxy-D-mannose
  作者：Hans Helmut Baer、Hermann O. L. Fischer

  DOI：10.1021/ja01499a060

  日期：1960.7