Ethyl (α-p-Methoxybenzyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D-glycero-non-7-eno-1,5-pyranos)uronate | 120927-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl (α-p-Methoxybenzyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D-glycero-non-7-eno-1,5-pyranos)uronate
• 英文别名: Ethyl [α-p-Methoxybenzyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D-glycero-non-7-eno-1,5-pyranos]uronate；ethyl (E,4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3R,4S,5S,6S)-5-iodo-6-[(4-methoxyphenyl)methoxy]-3,4-bis(phenylmethoxy)oxan-2-yl]but-2-enoate
• CAS: 120927-59-5
• 化学式: C₃₉H₅₁IO₈Si
• 分子量: 802.819
• InChiKey: IMOAKGHFFACECW-NGBXFIJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Ethyl (α-p-Methoxybenzyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D-glycero-non-7-eno-1,5-pyranos)uronate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 [(1S,3S,4S,5R,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester 、 [(1S,3S,4S,5R,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester
  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
• 作为产物：
  描述：

  D-葡萄烯糖 在 咪唑 、 lead(IV) acetate 、 N-碘代丁二酰亚胺 、 四氧化锇 、 4 A molecular sieve 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 sodium carbonate 、 N-甲基吗啉氧化物 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 21.5h， 生成 Ethyl (α-p-Methoxybenzyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D-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