(3aR,5S,6S,6aR)-2,2-dimethyl-5-[(2S)-(313C)oxiran-2-yl]-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole | 599196-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,5S,6S,6aR)-2,2-dimethyl-5-[(2S)-(313C)oxiran-2-yl]-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 599196-27-7
• 化学式: C₁₆H₂₀O₅
• 分子量: 293.321
• InChiKey: DLIZGFMSHQWPGV-OHQBFHMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6S,6aR)-2,2-dimethyl-5-[(2S)-(313C)oxiran-2-yl]-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 氢氧化钾 、 水 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 (1R)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl](213C)ethane-1,2-diol
  参考文献：
  名称：

  Practical synthesis of [1-13C]- and [6-13C]-d-galactose

  摘要：

  The chemical synthesis of C-13-labeled D-galactose as useful molecular probes for studying the conformation of oligosaccharides attached to proteins was performed. The method for synthesizing the title labeled compounds was newly developed via the corresponding 1-ene and 5-ene compounds derived from 1,2:5,6-di-O-isoproppylidene-alpha-D-galactofuranose by considering the efficient introduction of the atom. All protons of galactose from H-1 to H-6 were observed by the HMQC-HOHAHA technique using 1:1 mixtures of methyl [1-C-13]- and [6-C-13]-beta-D-galactopyranoside, which were prepared from the title compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01098-0
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 sodium periodate 、 正丁基锂 、 硼烷 、 水 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,5S,6S,6aR)-2,2-dimethyl-5-[(2S)-(313C)oxiran-2-yl]-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Practical synthesis of [1-13C]- and [6-13C]-d-galactose

  摘要：

  The chemical synthesis of C-13-labeled D-galactose as useful molecular probes for studying the conformation of oligosaccharides attached to proteins was performed. The method for synthesizing the title labeled compounds was newly developed via the corresponding 1-ene and 5-ene compounds derived from 1,2:5,6-di-O-isoproppylidene-alpha-D-galactofuranose by considering the efficient introduction of the atom. All protons of galactose from H-1 to H-6 were observed by the HMQC-HOHAHA technique using 1:1 mixtures of methyl [1-C-13]- and [6-C-13]-beta-D-galactopyranoside, which were prepared from the title compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01098-0