4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl ethanesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl ethanesulfonamide
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-(ethylsulfonylamino)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• 化学式: C₁₂H₁₉NO₇S
• 分子量: 321.351
• InChiKey: AHLWEJDBJZJGJF-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙基磺酰胺 、 乙酰化葡萄烯糖 在 fluoroboronic acid adsorbed on silica gel 作用下， 以 乙腈 为溶剂， 生成 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl ethanesulfonamide 、 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl ethanesulfonamide
  参考文献：
  名称：

  Synthesis of 2,3-Unsaturated O- and N-Glycosides by HBF4˙SiO2-Catalyzed Ferrier Rearrangement of d-Glycals

  摘要：

  氟硼酸吸附于硅胶上（HBF4⋅SiO2）催化佛雷尔重排反应，在醇和磺酰胺作用下生成2,3-不饱和的O-和N-糖苷，产率优良至极佳，并具有高度的α-立体选择性。

  DOI：

  10.1055/s-0028-1088105

文献信息

• Synthesis of 2,3-Unsaturated O- and N-Glycosides by HBF4˙SiO2-Catalyzed Ferrier Rearrangement of d-Glycals
  作者：Pedro Colinas、Oscar Rodríguez、Rodolfo Bravo

  DOI：10.1055/s-0028-1088105

  日期：2009.4

  Fluoroboronic acid adsorbed on silica gel (HBF4˙SiO2) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.

  氟硼酸吸附于硅胶上（HBF4⋅SiO2）催化佛雷尔重排反应，在醇和磺酰胺作用下生成2,3-不饱和的O-和N-糖苷，产率优良至极佳，并具有高度的α-立体选择性。
• Ferrier sulfonamidoglycosylation of d-glycals
  作者：Pedro A. Colinas、Rodolfo D. Bravo

  DOI：10.1016/j.carres.2007.06.027

  日期：2007.11

  A series of novel N-glycosyl sulfonamides were prepared via Ferrier sulfonamidoglycosylation of D-glycals with good to high alpha-stereo selectivity. Two new glycosylsulfamides were tested as carbonic anhydrase (CA II) inhibitors and showed good properties in the micromolar range. (C) 2007 Elsevier Ltd. All rights reserved.
• Efficient synthesis of 2,3-unsaturated sulfonamidoglycosides by Amberlyst 15
  作者：Carlos A. Témpera、Pedro A. Colinas、Rodolfo D. Bravo

  DOI：10.1016/j.tetlet.2010.07.076

  日期：2010.10

  Sulfonamidoglycosylation of D-glycals in the presence of Amberlyst 15 proceeded effectively to afford the sulfonamidoglycosides in good to high yields with minimal workup and short reaction times. Two N-glycosyl sulfonamides were tested as inhibitors of tumor cell growth in vitro and showed antiproliferative properties in the micromolar range. (C) 2010 Elsevier Ltd. All rights reserved.