1-[(3aS,4S,6R,6aR)-6-[(1R)-1,2-dihydroxy(213C)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazol-3-yl]ethanone | 561321-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(3aS,4S,6R,6aR)-6-[(1R)-1,2-dihydroxy(213C)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazol-3-yl]ethanone
• CAS: 561321-87-7
• 化学式: C₁₂H₂₁NO₆
• 分子量: 276.291
• InChiKey: SLBGHRNVLHUAKT-ROKDEQAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(3aS,4S,6R,6aR)-6-[(1R)-1,2-dihydroxy(213C)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazol-3-yl]ethanone 在 Dowex 50W (H⁺) 作用下， 以 水 为溶剂， 以85%的产率得到[6-13C]D-ManNAc
  参考文献：
  名称：

  Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN

  摘要：

  The chemoenzymatic synthesis of C-13-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was performed by using [6-C-13]-ManNAc, [6-C-13]-Man and [3-C-13]-pyruvic acid sodium salt. In the synthesis of the compounds, 5,6-anhydro intermediates were found to easily provide not only 6-C-13-labeled but also 5-, and 6-modified NeuAc and KDN analogs. Furthermore, it was demonstrated that identical results are obtained by NMR for both [3 ,9-C-13]-NeuAc and 1:1 mixtures of [3-C-13]- and [9-C-13]-NeuAc. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00690-7
• 作为产物：
  描述：

  Methyl 2-acetamido-2-deoxy-2,3-N,O-isopropyliden-α-D-mannofuranosid 在 氢氧化钾 、 sodium periodate 、 正丁基锂 、 四丁基氢氧化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 生成 1-[(3aS,4S,6R,6aR)-6-[(1R)-1,2-dihydroxy(213C)ethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazol-3-yl]ethanone
  参考文献：
  名称：

  Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN

  摘要：

  The chemoenzymatic synthesis of C-13-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was performed by using [6-C-13]-ManNAc, [6-C-13]-Man and [3-C-13]-pyruvic acid sodium salt. In the synthesis of the compounds, 5,6-anhydro intermediates were found to easily provide not only 6-C-13-labeled but also 5-, and 6-modified NeuAc and KDN analogs. Furthermore, it was demonstrated that identical results are obtained by NMR for both [3 ,9-C-13]-NeuAc and 1:1 mixtures of [3-C-13]- and [9-C-13]-NeuAc. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00690-7

文献信息

• Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN
  作者：Ken-ichi Sato、Shoji Akai、Toshiyuki Hiroshima、Hidenori Aoki、Mayumi Sakuma、Ken-ju Suzuki

  DOI：10.1016/s0040-4039(03)00690-7

  日期：2003.4

  The chemoenzymatic synthesis of C-13-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was performed by using [6-C-13]-ManNAc, [6-C-13]-Man and [3-C-13]-pyruvic acid sodium salt. In the synthesis of the compounds, 5,6-anhydro intermediates were found to easily provide not only 6-C-13-labeled but also 5-, and 6-modified NeuAc and KDN analogs. Furthermore, it was demonstrated that identical results are obtained by NMR for both [3 ,9-C-13]-NeuAc and 1:1 mixtures of [3-C-13]- and [9-C-13]-NeuAc. (C) 2003 Elsevier Science Ltd. All rights reserved.