methyl 3,4,6-tri-O-acetyl-2-bromodifluoromethyl-2-deoxy-β-D-glucopyranoside | 207342-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-2-bromodifluoromethyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-[bromo(difluoro)methyl]-6-methoxyoxan-2-yl]methyl acetate
• CAS: 207342-15-2
• 化学式: C₁₄H₁₉BrF₂O₈
• 分子量: 433.201
• InChiKey: KWGAJQCKDBYVJE-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-bromodifluoromethyl-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal [Co^III(dmgH)₂pyCl] 、 氢气 、 碘 、 氢化铝 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-C-(1,1-difluorononyl)-β-D-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
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 calcium sulfate 、 sodium dithionite 、 碳酸氢钠 、 silver carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl 3,4,6-tri-O-acetyl-2-bromodifluoromethyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A New Method for the Selective Introduction of Difluoromethyl and Trifluoromethyl Groups into Sugar Moieties

  摘要：

  We have studied the fluoroalkylation of the glucal 1 and the galactal 4 with dibromodifluoromethane via the 2-C-bromodifluoromethyl-substituted glycosyl bromides 2 and 5, respectively, followed by glycosylation to the methyl beta-D-glycosides 3 and 6. The bromodifluoromethyl groups in the 2 position of the compounds 3 and 6 were converted into difluoromethyl and trifluoromethyl groups, respectively, giving the fluorinated monosaccharides 7-10.

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<919::aid-ejoc919>3.0.co;2-3