cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-1-thio-α-D-pyranoside | 240418-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-1-thio-α-D-pyranoside
• 英文别名: [(2R,3S,6R)-3-acetyloxy-6-cyclohexylsulfanyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 240418-69-3
• 化学式: C₁₆H₂₄O₅S
• 分子量: 328.43
• InChiKey: QGNORDCGMARKOC-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环己硫醇 、 乙酰化葡萄烯糖 在 samarium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以81%的产率得到cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-1-thio-α-D-pyranoside
  参考文献：
  名称：

  Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals

  摘要：

  By using Sm(OTf)(3) as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-L-rhamnal under mild reaction conditions in good yield and high anomeric selectivity. It was found that under certain conditions, reaction of 3,4-di-O-acetyl-L-rhamnal with thiol leads to temperature-dependent formation of C-1-S and C-3-S product. A temperature-dependent profile of the yield of these two products is given. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.060

文献信息

• Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)–C(3) Unsaturated and α-<scp>d</scp>-Mannopyranosyl Sulfones
  作者：Sravanthi Chittela、Thurpu Raghavender Reddy、Palakodety Radha Krishna、Sudhir Kashyap

  DOI：10.1021/acs.joc.5b00975

  日期：2015.7.17

  An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and a-p-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access alpha-n-mannopyranosyl sulfones in good yields with high regioselectivity.
• RuCl3·3H2O as catalyst for Ferrier rearrangement: an efficient procedure for the preparation of pseudoglycosides
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.09.061

  日期：2013.11

  By using RuCl3 center dot 3H(2)O as catalyst, an improved method for the synthesis of 2,3-unsaturated-glycosides has been established. A series of 2, 3-unsaturated-glucosides were obtained from 2,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-6-deoxy-L-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• CF3SO3H–SiO2 as catalyst for Ferrier rearrangement: an efficient procedure for the synthesis of pseudoglycosides
  作者：Peiran Chen、Shaoshan Wang

  DOI：10.1016/j.tet.2012.11.019

  日期：2013.1

  An efficient method for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated glycosides by using triflic acid on SiO2 as catalyst has been established. A series of 2,3-unsaturated glucosides were synthesized in good yield and high anomeric selectivity under transition metal-free conditions. (c) 2012 Elsevier Ltd. All rights reserved.