(4S)-r-4,c-5-dihydroxy-t-6-[(5'S)-5'-(methoxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-N,N-dimethyl-1,2-oxazinane-2-carboxamide | 135587-82-5

• 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: (4S)-r-4,c-5-dihydroxy-t-6-[(5'S)-5'-(methoxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-N,N-dimethyl-1,2-oxazinane-2-carboxamide
• 英文别名: methyl (2S)-1-[(4S,5S,6S)-2-(dimethylcarbamoyl)-4,5-dihydroxyoxazinan-6-yl]-5-oxopyrrolidine-2-carboxylate
• CAS: 135587-82-5
• 化学式: C₁₃H₂₁N₃O₇
• 分子量: 331.326
• InChiKey: ZWINTQMKEOWPGT-UUTMEEIUSA-N

物化性质

• 熔点：
  171 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  549.6±50.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S)-r-4,c-5-dihydroxy-t-6-[(5'S)-5'-(methoxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-N,N-dimethyl-1,2-oxazinane-2-carboxamide 在 镍 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 Acetic acid (1S,2R)-2,3-diacetoxy-1-(3,3-dimethyl-ureidomethyl)-propyl ester
  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：

  methyl (2S)-1-[(6S)-2-(dimethylcarbamoyl)-3,6-dihydrooxazin-6-yl]-5-oxopyrrolidine-2-carboxylate 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 24.0h， 以40%的产率得到(4S)-r-4,c-5-dihydroxy-t-6-[(5'S)-5'-(methoxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-N,N-dimethyl-1,2-oxazinane-2-carboxamide
  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.