3-deoxy-3-(N-cyclopentylthiocarboxamido)-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose | 195315-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-(N-cyclopentylthiocarboxamido)-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose
• CAS: 195315-76-5
• 化学式: C₁₇H₂₈N₂O₅S
• 分子量: 372.486
• InChiKey: WIDQQOIUPLRKII-MPZWGZMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  92.21
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 3-deoxy-3-(N-cyclopentylthiocarboxamido)-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以89%的产率得到5,6-bis(O-tert-butyldimethylsilyl)-3-(N-cyclopentylthiocarboxamido)-3-deoxy-1,2-O-isopropylidene-3-C-vinyl-α-D-glucofuranose
  参考文献：
  名称：

  Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin

  摘要：

  A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-alpha-D-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.032
• 作为产物：
  描述：

  [(3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-acetic acid methyl ester 在 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 、 xylene 为溶剂， 反应 4.0h， 生成 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