t-butyl (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate | 529483-99-6

• 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: t-butyl (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate
• 英文别名: tert-butyl (4S,5S,6S)-4,5-dihydroxy-6-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-5-oxopyrrolidin-1-yl]oxazinane-2-carboxylate
• CAS: 529483-99-6
• 化学式: C₁₈H₃₀N₂O₈
• 分子量: 402.445
• InChiKey: GXXIARXUHLYTKT-IMIFBBOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  t-butyl (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate 在 二氧化硫 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 144.0h， 以76%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
• 作为产物：
  描述：

  N-羟基氨基甲酸叔丁酯 在 四氧化锇 、 N-甲基吲哚酮 、 benzyltrimethylammonium periodate 作用下， 以 甲醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 25.0h， 生成 t-butyl (4S)-t-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-r-4,c-5-dihydroxy-1,2-oxazinane-2-carboxylate
  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.