Methanesulfonic acid 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]-ethyl ester | 195315-72-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid 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]-ethyl ester
• CAS: 195315-72-1
• 化学式: C₂₄H₄₈O₈SSi₂
• 分子量: 552.877
• InChiKey: DWRQIIURGGUZDV-UXUBXMIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 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]-ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 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
• 作为产物：
  描述：

  methyl (2E)-2-[(3aR,5S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-ylidene]acetate 在 咪唑 、 二异丁基氢化铝 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 Methanesulfonic acid 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]-ethyl ester
  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