(3aS,4S,6R,6aS)-6-(213C)ethenyl-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole | 561321-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6R,6aS)-6-(213C)ethenyl-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 561321-75-3
• 化学式: C₁₆H₂₀O₄
• 分子量: 277.321
• InChiKey: HEXNNOXWSMXKLK-LKPUSSOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,6aS)-6-(213C)ethenyl-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 在 氢氧化钾 、 四丁基氢氧化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (1R)-1-[(3aS,4S,6R,6aS)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl](213C)ethane-1,2-diol
  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：

  苄基2,3-O-异亚丙基呋喃己糖i去 在 sodium periodate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (3aS,4S,6R,6aS)-6-(213C)ethenyl-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
  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