(2-deoxy-3,4-di-O-pivaloyl-β-D-threo-pentopyranosyl)-chlorodifluoromethane | 917378-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2-deoxy-3,4-di-O-pivaloyl-β-D-threo-pentopyranosyl)-chlorodifluoromethane
• 英文别名: [(2R,4R,5R)-2-[chloro(difluoro)methyl]-5-(2,2-dimethylpropanoyloxy)oxan-4-yl] 2,2-dimethylpropanoate
• CAS: 917378-87-1
• 化学式: C₁₆H₂₅ClF₂O₅
• 分子量: 370.821
• InChiKey: XJDQWTJAYVCMOB-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-deoxy-3,4-di-O-pivaloyl-β-D-threo-pentopyranosyl)-chlorodifluoromethane 、 烯丙基三丁基锡 以 乙酸乙酯 为溶剂， 以62%的产率得到4,4-difluoro-4-(2-deoxy-3,4-di-O-pivaloyl-β-D-threo-pentopyranosyl)-butene
  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：

  甲醇 、 二氟一氯溴甲烷 、 di-O-(trimethylacetyl)-D-xylal 在 sodium dithionite 、 碳酸氢钠 作用下， 反应 9.0h， 以22%的产率得到methyl 2-C-chlorodifluoromethyl-2-deoxy-3,4-di-O-pivaloyl-D-xylopyranoside
  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

文献信息

• Chlorodifluoromethyl-substituted monosaccharide derivatives—radical activation of the carbon–chlorine-bond
  作者：Anita Wegert、Martin Hein、Helmut Reinke、Norbert Hoffmann、Ralf Miethchen

  DOI：10.1016/j.carres.2006.08.023

  日期：2006.11

  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.