1,5-anhydro-2-deoxy-3,4:6,7-di-O-isopropylidene-1-C-(4-methoxyphenyl)-D-manno-hept-1-enitol | 1351958-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,5-anhydro-2-deoxy-3,4:6,7-di-O-isopropylidene-1-C-(4-methoxyphenyl)-D-manno-hept-1-enitol
• 英文别名: (3aR,4R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(4-methoxyphenyl)-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 1351958-15-0
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: PTAWBVPADJZTEM-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-deoxy-3,4:6,7-di-O-isopropylidene-1-C-(4-methoxyphenyl)-D-manno-hept-1-enitol 在 sodium periodate 、 偶氮二异丁腈 、 ruthenium(III) trichloride hydrate 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 8.67h， 生成 methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-β-D-manno-2-octulopyranosidonic acid
  参考文献：
  名称：

  Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo Glycoside Synthesis

  摘要：

  A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-beta-D-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding beta-Kdo glycosides. A mechanism for the stereoselective formation of beta-D-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.

  DOI：

  10.1021/jo201531j
• 作为产物：
  描述：

  (3aS,4R,6R,7R,7aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-iodo-6-(4-methoxyphenyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以80%的产率得到1,5-anhydro-2-deoxy-3,4:6,7-di-O-isopropylidene-1-C-(4-methoxyphenyl)-D-manno-hept-1-enitol
  参考文献：
  名称：

  Unexpected Anomeric Selectivity of a 1-C-Arylglycal Donor in Kdo Glycoside Synthesis

  摘要：

  A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-beta-D-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding beta-Kdo glycosides. A mechanism for the stereoselective formation of beta-D-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.

  DOI：

  10.1021/jo201531j

文献信息

• Unexpected Anomeric Selectivity of a 1-<i>C</i>-Arylglycal Donor in Kdo Glycoside Synthesis
  作者：Yuxin Qian、Jianhao Feng、Masood Parvez、Chang-Chun Ling

  DOI：10.1021/jo201531j

  日期：2012.1.6

  A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-beta-D-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding beta-Kdo glycosides. A mechanism for the stereoselective formation of beta-D-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.