(1R,4S,5R,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-thiabicyclo[2.2.1]heptan-3-one | 384341-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: (1R,4S,5R,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-thiabicyclo[2.2.1]heptan-3-one
• 英文别名: (1R,4S,5R,6R)-5,6-bis[[tert-butyl(dimethyl)silyl]oxy]-2-thiabicyclo[2.2.1]heptan-3-one
• CAS: 384341-77-9
• 化学式: C₁₈H₃₆O₃SSi₂
• 分子量: 388.719
• InChiKey: OBHDJIKOEYWADT-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4S,5R,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-thiabicyclo[2.2.1]heptan-3-one 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以74%的产率得到(1R,2R,3R,5R)-1,2-di-O-(tert-butyldimethylsilanyl)-5-hydroxymethyl-3-mercaptocyclopentane-1,2-diol
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-d-Xylo, β-d-Ribo, β-l-Arabino, and β-l-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols

  摘要：

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

  DOI：

  10.1021/jo010585v
• 作为产物：
  描述：

  在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 silica gel 、 溶剂黄146 、 N,N-二异丙基乙胺 、 nickel dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 (1R,4S,5R,6R)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-thiabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-d-Xylo, β-d-Ribo, β-l-Arabino, and β-l-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols

  摘要：

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

  DOI：

  10.1021/jo010585v