4-amino-1,4-dideoxy-L-erythrose-1-sulfonic acid | 529484-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-amino-1,4-dideoxy-L-erythrose-1-sulfonic acid
• 英文别名: (2R,3S,4S)-3,4-dihydroxypyrrolidine-2-sulfonic acid
• CAS: 529484-05-7
• 化学式: C₄H₉NO₅S
• 分子量: 183.185
• InChiKey: JQOLKMFBRBFUIO-YVZJFKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  11
• 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：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-1,4-dideoxy-L-erythrose-1-sulfonic acid 在 barium dihydroxide 、 重水 作用下， 以 重水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose

  摘要：

  Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-L-erythrose and 4-amino-5-deoxy-L-ribose series were synthesised by asymmetric hetero-Diels-Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-L-erythrose and 4-amino-4,5-dideoxy-L-ribose were potent beta-D-glucosidase, alpha-D-mannosidase, alpha- and beta-D-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of alpha-D-mannosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01512-0
• 作为产物：
  描述：

  (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane 在 二氧化硫 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 144.0h， 以87%的产率得到4-amino-1,4-dideoxy-L-erythrose-1-sulfonic acid
  参考文献：
  名称：

  Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose

  摘要：

  Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-L-erythrose and 4-amino-5-deoxy-L-ribose series were synthesised by asymmetric hetero-Diels-Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-L-erythrose and 4-amino-4,5-dideoxy-L-ribose were potent beta-D-glucosidase, alpha-D-mannosidase, alpha- and beta-D-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of alpha-D-mannosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01512-0

文献信息

• Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose
  作者：Jean-Bernard Behr、Carine Chevrier、Albert Defoin、Céline Tarnus、Jacques Streith

  DOI：10.1016/s0040-4020(02)01512-0

  日期：2003.1

  Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-L-erythrose and 4-amino-5-deoxy-L-ribose series were synthesised by asymmetric hetero-Diels-Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-L-erythrose and 4-amino-4,5-dideoxy-L-ribose were potent beta-D-glucosidase, alpha-D-mannosidase, alpha- and beta-D-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of alpha-D-mannosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.