n-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 1192736-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: n-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threohex-2-enopyranoside；[(2R,3R,6S)-3-acetyloxy-6-butoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1192736-24-5
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: OINLLWWLEJQYMS-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-三乙酰半乳糖烯 、 正丁醇 在 carbon immobilized iron (III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以93%的产率得到n-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  FeCl₃·6H₂O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-UnsaturatedO-andS-Glycosides

  摘要：

  DOI：

  10.1080/07328303.2014.941995

文献信息

• 3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
  作者：Naganjaneyulu Bodipati、Srinivasa Rao Palla、Venkateshwarlu Komera、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2014.10.093

  日期：2014.12

  A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.

  描述了一种简单的程序，用于在乙腈中合成2,3-不饱和糖苷以及在3,5-二硝基苯甲酸存在下在二氯甲烷中将醇和酚进行四氢吡喃基化。使多种醇和硫醇与缩醛反应，以高收率和高α选择性得到所需产物。
• Scope of AuCl3 in the activation of per-O-acetylglycals
  作者：Rengarajan Balamurugan、Srinivasa Rao Koppolu

  DOI：10.1016/j.tet.2009.07.087

  日期：2009.9

  Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make beta-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product. (C) 2009 Elsevier Ltd. All rights reserved.