Ethyl (α-Methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate | 137792-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl (α-Methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate
• 英文别名: Ethyl [α-Methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D,L-glycero-non-7-eno-1,5-pyranos]uronate；ethyl (E)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3R,4S,5S,6S)-5-iodo-6-methoxy-3,4-bis(phenylmethoxy)oxan-2-yl]but-2-enoate
• CAS: 137792-61-1；137792-81-5
• 化学式: C₃₂H₄₅IO₇Si
• 分子量: 696.695
• InChiKey: NJZKHGPNYYGTTQ-HXJJUNKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  α-Methyl 3,4-Di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D,L-glycero-oct-7-eno-1,5-pyranoside 在 lead(IV) acetate 、 四氧化锇 、 sodium hydride 、 sodium carbonate 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 0.5h， 生成 Ethyl (α-Methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033