(2R,3R,4R)-4-[(2S,3R,4S,5R,6R)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-yn-2-ol | 330189-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R)-4-[(2S,3R,4S,5R,6R)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-yn-2-ol
• CAS: 330189-32-7
• 化学式: C₅₀H₆₉IO₆Si₃
• 分子量: 977.255
• InChiKey: JXMZTJYYJOQONU-ILUBASFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.21
• 重原子数：
  60.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-4-[(2S,3R,4S,5R,6R)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-yn-2-ol 在 六羰基钨 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以61%的产率得到(2R,3R,4R)-4-[(2S,3R,4S,5R,6R)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Discovery of the tungsten carbonyl-catalyzed endo-selective alkynyl alcohol cycloisomerization reaction: applications to stereoselective syntheses of d-olivose, d-olivose disaccharide substructures of landomycin and mithramycin

  摘要：

  An account of the discovery of the tungsten carbonyl-catalyzed endo-selective cycloisomerization of alkynyl alcohols to dihydropyrans is described. The utility of this new chemical transformation involving tungsten vinylidene catalytic intermediates is demonstrated in stereoselective syntheses of disaccharide substructures 26-28 of the landomycin and mithramycin families of anticancer antibiotics. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00643-4
• 作为产物：
  描述：

  Benzoic acid (1R,2R,3R)-3-[(2S,3R,4S,5R,6R)-4,5-bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到(2R,3R,4R)-4-[(2S,3R,4S,5R,6R)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-hex-5-yn-2-ol
  参考文献：
  名称：

  Discovery of the tungsten carbonyl-catalyzed endo-selective alkynyl alcohol cycloisomerization reaction: applications to stereoselective syntheses of d-olivose, d-olivose disaccharide substructures of landomycin and mithramycin

  摘要：

  An account of the discovery of the tungsten carbonyl-catalyzed endo-selective cycloisomerization of alkynyl alcohols to dihydropyrans is described. The utility of this new chemical transformation involving tungsten vinylidene catalytic intermediates is demonstrated in stereoselective syntheses of disaccharide substructures 26-28 of the landomycin and mithramycin families of anticancer antibiotics. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00643-4