(2R,4S,2'S,4'R)-2-benzyloxymethyl-6-[2',4'-bis(tert-butyldimethylsilanyloxy)-6'-(4-methoxy-benzyloxy)-hexyl]-4-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran | 474745-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4S,2'S,4'R)-2-benzyloxymethyl-6-[2',4'-bis(tert-butyldimethylsilanyloxy)-6'-(4-methoxy-benzyloxy)-hexyl]-4-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran
• 英文别名: tert-butyl-[(2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(4-methoxyphenyl)methoxy]-1-[(2R,4S)-4-[(4-methoxyphenyl)methoxy]-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-6-yl]hexan-2-yl]oxy-dimethylsilane
• CAS: 474745-97-6
• 化学式: C₄₇H₇₂O₈Si₂
• 分子量: 821.255
• InChiKey: NCXYTEGIDKOPOK-WWTFGTEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.65
• 重原子数：
  57
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4S,2'S,4'R)-2-benzyloxymethyl-6-[2',4'-bis(tert-butyldimethylsilanyloxy)-6'-(4-methoxy-benzyloxy)-hexyl]-4-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol
  参考文献：
  名称：

  Diastereoselective Synthesis of the C(17)−C(28) Fragment (The C−D Spiroketal Unit) of Spongistatin 1 (Altohyrtin A) via a Kinetically Controlled Iodo-Spiroketalization Reaction

  摘要：

  [GRAPHIC]A convergent and stereocontrolled synthesis of spiroketal 15 corresponding to the C-D fragment of spongistatin 1 has been accomplished by a sequence utilizing a kinetically controlled intramolecular iodo-spiroketalization of glycal 2, which in turn was synthesized via a ring-closing metathesis reaction.

  DOI：

  10.1021/ol0266875
• 作为产物：
  描述：

  (3R)-methyl-3-hydroxy-5-[(4-methoxybenzyl)oxy]pentanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 2,2-dimethyl-2-butene 、 2,4,6-三氯苯甲酰氯 、 二异丁基氢化铝 、 三乙胺 、 二异丙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 83.0h， 生成 (2R,4S,2'S,4'R)-2-benzyloxymethyl-6-[2',4'-bis(tert-butyldimethylsilanyloxy)-6'-(4-methoxy-benzyloxy)-hexyl]-4-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Diastereoselective Synthesis of the C(17)−C(28) Fragment (The C−D Spiroketal Unit) of Spongistatin 1 (Altohyrtin A) via a Kinetically Controlled Iodo-Spiroketalization Reaction

  摘要：

  [GRAPHIC]A convergent and stereocontrolled synthesis of spiroketal 15 corresponding to the C-D fragment of spongistatin 1 has been accomplished by a sequence utilizing a kinetically controlled intramolecular iodo-spiroketalization of glycal 2, which in turn was synthesized via a ring-closing metathesis reaction.

  DOI：

  10.1021/ol0266875

文献信息

• Diastereoselective Synthesis of the C(17)−C(28) Fragment (The C−D Spiroketal Unit) of Spongistatin 1 (Altohyrtin A) via a Kinetically Controlled Iodo-Spiroketalization Reaction
  作者：Edward B. Holson、William R. Roush

  DOI：10.1021/ol0266875

  日期：2002.10.1

  [GRAPHIC]A convergent and stereocontrolled synthesis of spiroketal 15 corresponding to the C-D fragment of spongistatin 1 has been accomplished by a sequence utilizing a kinetically controlled intramolecular iodo-spiroketalization of glycal 2, which in turn was synthesized via a ring-closing metathesis reaction.