3,3'-(2,3,4,6-tetra-O-acetyl-D-mannopyranosylidene)bis(1-propene) | 369397-17-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3'-(2,3,4,6-tetra-O-acetyl-D-mannopyranosylidene)bis(1-propene)
• 英文别名: [(2R,3R,4S,5S)-3,4,5-triacetyloxy-6,6-bis(prop-2-enyl)oxan-2-yl]methyl acetate
• CAS: 369397-17-1
• 化学式: C₂₀H₂₈O₉
• 分子量: 412.437
• InChiKey: KSQUXJCGJVVLCW-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,3'-(2,3,4,6-tetra-O-acetyl-D-mannopyranosylidene)bis(1-propene) 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以89%的产率得到2,3,4,6-tetra-O-acetylspiro[1,5-anhydro-D-mannitol-1,4'-cyclopent-1'-ene]
  参考文献：
  名称：

  Ring-Closing Olefin Metathesis of 3,3′-(D-Glycopyranosylidene)bis(1-propene) Compounds as a Route to Anomeric Spiro Sugars

  摘要：

  New peracetylated 3,3 '-(D-glycopyranosylidene)bis(1-propene), prepared from peracetylated anomeric sugar dihalides and allyltributyltin in excess under UV irradiation conditions (AIBN, ca. 35 degreesC), lent themselves to ring-closing olefin metathesis in the presence of Grubbs' catalyst (6 mol %) to afford the corresponding peracetylated spiro[1,5-anhydro-D-glycopyranositol-1,4 ' -cyclopent-1 ' -enes] (D-gluco: 81%, D-Manno: 89%, D-galacto: 72% isolated yield), which could be deacetylated quantitatively. The bis(allylation) reaction (D-gluco: 40%, D-manno: 34%, D-galacto: 24% isolated yield) was in competition with radical-induced rearrangement and elimination reactions. The last process, found to be favored at higher temperature (80 degreesC), opens an easy route to sugar dienes difficult to prepare otherwise.

  DOI：

  10.1002/1099-0690(200108)2001:15<2939::aid-ejoc2939>3.0.co;2-h
• 作为产物：
  描述：

  烯丙基三丁基锡 、 2,3,4,6-Tetra-O-acetyl-1-chloro-D-mannosyl bromide 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 2.5h， 以34%的产率得到3,3'-(2,3,4,6-tetra-O-acetyl-D-mannopyranosylidene)bis(1-propene)
  参考文献：
  名称：

  Ring-Closing Olefin Metathesis of 3,3′-(D-Glycopyranosylidene)bis(1-propene) Compounds as a Route to Anomeric Spiro Sugars

  摘要：

  New peracetylated 3,3 '-(D-glycopyranosylidene)bis(1-propene), prepared from peracetylated anomeric sugar dihalides and allyltributyltin in excess under UV irradiation conditions (AIBN, ca. 35 degreesC), lent themselves to ring-closing olefin metathesis in the presence of Grubbs' catalyst (6 mol %) to afford the corresponding peracetylated spiro[1,5-anhydro-D-glycopyranositol-1,4 ' -cyclopent-1 ' -enes] (D-gluco: 81%, D-Manno: 89%, D-galacto: 72% isolated yield), which could be deacetylated quantitatively. The bis(allylation) reaction (D-gluco: 40%, D-manno: 34%, D-galacto: 24% isolated yield) was in competition with radical-induced rearrangement and elimination reactions. The last process, found to be favored at higher temperature (80 degreesC), opens an easy route to sugar dienes difficult to prepare otherwise.

  DOI：

  10.1002/1099-0690(200108)2001:15<2939::aid-ejoc2939>3.0.co;2-h