(R)-1-((3aR,5S,6S,6aR)-6-Isothiocyanato-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol | 195315-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((3aR,5S,6S,6aR)-6-Isothiocyanato-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol
• CAS: 195315-75-4
• 化学式: C₁₂H₁₇NO₅S
• 分子量: 287.337
• InChiKey: LBJHMAUZUGBCFW-GPTQDWHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.51
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  环戊胺 、 (R)-1-((3aR,5S,6S,6aR)-6-Isothiocyanato-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 以 乙醚 为溶剂， 以94%的产率得到3-deoxy-3-(N-cyclopentylthiocarboxamido)-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose
  参考文献：
  名称：

  Stereocontrol by intrinsic antiparallel double repulsion on diacetone-D-glucose template. Diastereoselective synthesis of 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates

  摘要：

  A stereoselective synthesis of the branched-chain sugar 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. The side chain at C-4 of the substrates 4-Z, 4-E and 8-E is not a decisive factor for stereocontrol in the (3,3)-sigmatropic rearrangement of allylic thiocyanates, and the 1,2-O-isopropylidene group in each isomer profoundly affects the direction of the rearrangement. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01246-x
• 作为产物：
  描述：

  3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-(Z)-(2-thiocyanatoethylidene)-α-D-glucofuranose 在 三氟乙酸 作用下， 以 水 、 xylene 为溶剂， 反应 3.5h， 生成 (R)-1-((3aR,5S,6S,6aR)-6-Isothiocyanato-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol
  参考文献：
  名称：

  Stereocontrol by intrinsic antiparallel double repulsion on diacetone-D-glucose template. Diastereoselective synthesis of 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates

  摘要：

  A stereoselective synthesis of the branched-chain sugar 3(S)-isothiocyanato-3-deoxy-3-C-vinyl glucose via (3,3)-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. The side chain at C-4 of the substrates 4-Z, 4-E and 8-E is not a decisive factor for stereocontrol in the (3,3)-sigmatropic rearrangement of allylic thiocyanates, and the 1,2-O-isopropylidene group in each isomer profoundly affects the direction of the rearrangement. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01246-x