1,2:5,6-di-O-cyclohexylidene-3-O<(methylthio)thiocarbonyl>-α-D-glucofuranose | 129395-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-cyclohexylidene-3-O<(methylthio)thiocarbonyl>-α-D-glucofuranose
• 英文别名: 1,2:5,6-di-O-cyclohexylidene-3-O-methylthiothiocarbonyl-α-D-glucofuranose；O-[(3aR,5R,6S,6aR)-5-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-yl] methylsulfanylmethanethioate
• CAS: 129395-40-0
• 化学式: C₂₀H₃₀O₆S₂
• 分子量: 430.587
• InChiKey: GEPBNFATEYCDDR-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-cyclohexylidene-3-O<(methylthio)thiocarbonyl>-α-D-glucofuranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以63.6%的产率得到3,6-anhydro-5-O-methylthiothiocarbonyl-1,2-O-cyclohexylidene-α-D-glucofuranose
  参考文献：
  名称：

  3-O-Acyl triggered tandem Lewis acid catalyzed intramolecular cyclization of diacetone glucose derivatives to 5-O-acyl-3,6-anhydro-d-glucose

  摘要：

  BF(3) mediated one-pot conversion of 3-O-acyl-D-glucose-1,2:5,6-diacetonide derivatives to 5-O-acyl-3,6-anhydro-D-glucose is described through a tandem selective intramolecular cyclization sequence. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.034
• 作为产物：
  描述：

  二硫化碳 、 1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖 、 碘甲烷 在 sodium hydroxide 作用下， 生成 1,2:5,6-di-O-cyclohexylidene-3-O<(methylthio)thiocarbonyl>-α-D-glucofuranose
  参考文献：
  名称：

  Suryawanshi, S.N.; Rani, A.; Bhakuni, D.S., Synthetic Communications, 1990, vol. 20, # 5, p. 625 - 632

  摘要：

  DOI：

文献信息

• Radical cation reactions associated with the thiocarbonyl group
  作者：Derek H.R. Barton、Peter I. Dalko、Stephan D. Géro

  DOI：10.1016/s0040-4039(00)74167-0

  日期：1992.3

  The radical cation reactions of different thiocarbonyl compounds were examined. Compounds 7, 8, 11, 14 and 18 underwent a radical cation fragmentation in a photoinduced electron transfer (PET) reaction, in the presence of tris(4-bromophenyl)aminium hexachloroantimonate.

  检查了不同的硫代羰基化合物的自由基阳离子反应。化合物7，8，11，14和18在一个光诱导电子转移（PET）反应进行自由基阳离子碎裂，在三（4-溴苯基）六氯锑酸铵的存在。
• Suryawanshi, S.N.; Rani, A.; Bhakuni, D.S., Synthetic Communications, 1990, vol. 20, # 5, p. 625 - 632
  作者：Suryawanshi, S.N.、Rani, A.、Bhakuni, D.S.

  DOI：——

  日期：——
• 3-O-Acyl triggered tandem Lewis acid catalyzed intramolecular cyclization of diacetone glucose derivatives to 5-O-acyl-3,6-anhydro-d-glucose
  作者：Rajashaker Bantu、Hari Babu Mereyala、Lingaiah Nagarapu、Srinivas Kantevari

  DOI：10.1016/j.tetlet.2011.07.034

  日期：2011.9

  BF(3) mediated one-pot conversion of 3-O-acyl-D-glucose-1,2:5,6-diacetonide derivatives to 5-O-acyl-3,6-anhydro-D-glucose is described through a tandem selective intramolecular cyclization sequence. (C) 2011 Elsevier Ltd. All rights reserved.