dodecanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside | 557104-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: dodecanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside
• 英文别名: dodecyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside；[(2R,3S,6R)-3-acetyloxy-6-dodecylsulfanyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 557104-57-1
• 化学式: C₂₂H₃₈O₅S
• 分子量: 414.607
• InChiKey: PXJHMADBMIPZME-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  乙酰化葡萄烯糖 、 十二硫醇 在 sodium hydrogen sulfate 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以65%的产率得到dodecanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-1-thiohex-2-enopyranoside
  参考文献：
  名称：

  NaHSO（4）负载在硅胶上：糖的Ferrier重排的另一种催化剂。

  摘要：

  载于硅胶上的NaHSO（4）催化3,4,6-tri-O-乙酰基-D-葡萄糖与醇和硫醇的Ferrier重排反应，得到相应的2,3-不饱和糖苷，其端基异构体选择性高，且对反应时间短，产率极高。

  DOI：

  10.1016/j.carres.2011.08.023

文献信息

• 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
  作者：Peiran Chen、Dalin Zhang

  DOI：10.1016/j.tet.2014.09.060

  日期：2014.11

  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.