4-nitro-benzoic acid (3aR,5R,6R,7R,7aS)-7-benzyloxy-5-hydroxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran-6-yl ester | 776313-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitro-benzoic acid (3aR,5R,6R,7R,7aS)-7-benzyloxy-5-hydroxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran-6-yl ester
• CAS: 776313-89-4
• 化学式: C₂₃H₂₄INO₈
• 分子量: 569.35
• InChiKey: JDMPEDOUIGZCQG-XKYVVYCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  117.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-nitro-benzoic acid (3aR,5R,6R,7R,7aS)-7-benzyloxy-5-hydroxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran-6-yl ester 在 叠氮化四丁基铵 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 butyl-carbamic acid (3aR,5R,6R,7R,7aS)-7-benzyloxy-5-hydroxymethyl-2-[(3-phenyl-propionylamino)-methyl]-hexahydro-furo[3,2-b]pyran-6-yl ester
  参考文献：
  名称：

  Bicyclic carbohydrate-derived scaffolds for combinatorial libraries

  摘要：

  A bicyclic scaffold derived from the natural monosaccharide D-glucose, and possessing several diversity sites, was linked to various resins through the primary (C-6) hydroxyl and decorated on the solid phase: the hydroxyl group at C-4 was functionalized as ester, ether, and carbamate, the amino group ill the second cycle (C-3' position) was functionalized as amide, sulfonamide, and ureido- and thioureido-derivatives. The compounds synthesized oil the solid phase were tested for their antiproliferative activity oil tumor cell lines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.055
• 作为产物：
  描述：

  3-[2',3'-di-O-benzyl-4'-O-(4-nitrobenzoyl)-α-D-glucopyranosyl]-1-propene 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以61%的产率得到4-nitro-benzoic acid (3aR,5R,6R,7R,7aS)-7-benzyloxy-5-hydroxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran-6-yl ester
  参考文献：
  名称：

  Bicyclic carbohydrate-derived scaffolds for combinatorial libraries

  摘要：

  A bicyclic scaffold derived from the natural monosaccharide D-glucose, and possessing several diversity sites, was linked to various resins through the primary (C-6) hydroxyl and decorated on the solid phase: the hydroxyl group at C-4 was functionalized as ester, ether, and carbamate, the amino group ill the second cycle (C-3' position) was functionalized as amide, sulfonamide, and ureido- and thioureido-derivatives. The compounds synthesized oil the solid phase were tested for their antiproliferative activity oil tumor cell lines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.055