(3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-thiocyanato-eth-(E)-ylidene]-tetrahydro-furo[2,3-d][1,3]dioxole | 195315-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-thiocyanato-eth-(E)-ylidene]-tetrahydro-furo[2,3-d][1,3]dioxole
• 英文别名: [(2E)-2-[(3aR,5S,6aR)-5-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ylidene]ethyl] thiocyanate
• CAS: 195315-73-2
• 化学式: C₂₄H₄₅NO₅SSi₂
• 分子量: 515.862
• InChiKey: XQJHUXCYIVJUNU-XZKRWWPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-thiocyanato-eth-(E)-ylidene]-tetrahydro-furo[2,3-d][1,3]dioxole 以 xylene 为溶剂， 反应 4.0h， 以88%的产率得到5,6-bis(O-tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-3-isothiocyanato-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：

  2-[(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]-ethanol 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (3aR,5S,6aR)-5-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-thiocyanato-eth-(E)-ylidene]-tetrahydro-furo[2,3-d][1,3]dioxole
  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