methyl 3,4-di-O-acetyl-2-C-difluoromethyl-2,6-dideoxy-α-L-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2-C-difluoromethyl-2,6-dideoxy-α-L-glucopyranoside
• 英文别名: [(2S,3S,4S,5S,6R)-4-acetyloxy-5-(difluoromethyl)-6-methoxy-2-methyloxan-3-yl] acetate
• 化学式: C₁₂H₁₈F₂O₆
• 分子量: 296.268
• InChiKey: DRIFFIDSALZLKU-UUFGTPLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 偶氮二异丁腈 sodium dithionite 、 三正丁基氢锡 、 碳酸氢钠 、 乙烯基乙醚 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 methyl 3,4-di-O-acetyl-2-C-difluoromethyl-2,6-dideoxy-α-L-glucopyranoside
  参考文献：
  名称：

  Chlorodifluoromethyl-substituted monosaccharide derivatives—radical activation of the carbon–chlorine-bond

  摘要：

  The dithionite-mediated addition of BrCF2Cl to 3,4-di-O-pivaloyl-D-xylal (1) generated preferably 1-CF2Cl-substituted products, that is, (2-bromo-2-deoxy-3,4-di-O-pivaloyl-beta-D-xylopyranosyl)-chlorodifluoromethane and (2-deoxy-3,4-di-O-pivaloyl-beta-D-threo-pentopyranosyl)-chlorodifluoromethane. Selected chlorodifluorornethyl-substituted monosaccharide derivatives were hydrodechlorinated or alkylated at the CF2Cl-group using tin reagents under radical reaction conditions. Thus, hydrodechlorinations of (2,3,4-tri-O-acetyl-6-deoxy-alpha-L-gal actopyranosyl)-chlorodifluoromethane and of methyl 3,4-di-O-acetyl-2-C-chlorodifluoromethyl-2,6-dideoxy-alpha/beta-L-glucopyranoside are reported using tri-n-butyltin hydride initiated by AIBN. UV-initiated allylations are reported for reactions of (2-deoxy-3,4-di-O-pivaloyl-beta-D-threo-pentopyranosyl)-chlorodifluoromethane, (2,3,4-tri-O-acetyl-6-deoxy-alpha-L-galactopyranosyl)-chlorodifluoromethane, 1,3,4,6-tetra-O-acetyl-2-C-chlorodifluoromethyl-2-deoxy-alpha-D-glucopyranose, 1,3,4,6-tetra-O-acetyl-2-C-chlorodifluoromethyl-2-deoxy-alpha-D-mannopyranose and methyl 3,4-di-O-acetyl-2-C-chlorodifluoromethyl-2-deoxy-alpha/beta-D-rabinopyranoside with allyltri-n-butyltin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.023