(2S,6R)-1-(tosyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylheptane | 92934-90-2

• 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: (2S,6R)-1-(tosyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylheptane
• 英文别名: (2S,6R)-2,6-dimethyl-7-(tert-butyldimethylsilyloxyheptyl) p-toluenesulfonate；[(2S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylheptyl] 4-methylbenzenesulfonate
• CAS: 92934-90-2
• 化学式: C₂₂H₄₀O₄SSi
• 分子量: 428.709
• InChiKey: CZNJOUHIJGDBRH-VQTJNVASSA-N

物化性质

• 沸点：
  480.0±28.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-1-(tosyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylheptane 在 dilithium tetrachlorocuprate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2R^*,6R^*)-2,6,10-trimethylundecan-1-ol
  参考文献：
  名称：

  1,5-Acyclic stereoselection. The stereocontrolled synthesis of optically active vitamin E fourteen-carbon side chain alcohol

  摘要：

  Diels-Alder产物3首先转化为对称的九元环碳酸酯8。8与l-(−)-α-甲基苄胺（12）反应生成了光学活性的二对映异构尿素衍生物9a（9，R = H，R′ = C6H5CHCH3NHCO—）和9b（9，R = C6H5CHCH3NHCO—，R′ = H），分离并分别转化为11a和11b。化合物11a和11b随后分别转化为维生素E（1）的光学活性侧链醇2（R = H）。

  DOI：

  10.1139/v84-267
• 作为产物：
  描述：

  2,6-dimethyl-1,7-heptanediol 在 吡啶 、 4-二甲氨基吡啶 、 Pseudomonas cepacia lipase 、 1,1,2,3-四甲基胍 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 103.0h， 生成 (2S,6R)-1-(tosyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethylheptane
  参考文献：
  名称：

  Enzymatic Desymmetrization of meso-2,6-Dimethyl-1,7-heptanediol. Enantioselective Formal Synthesis of the Vitamin E Side Chain and the Insect Pheromone Tribolure

  摘要：

  The chiral syn-1,5-dimethylalkyl subunit is found in many natural products with significant biological activities. Enzymatic esterification of meso-2,6-dimethyl-1,7-heptanediol with isopropenyl acetate in the presence of Pseudomonas cepacia lipase in organic medium provided the chiral nonracemic monoester in high enantiomeric excess (ee = 95%). This chiral building block was used in the formal syntheses of vitamin E side chain and the insect pheromone tribolure.

  DOI：

  10.1021/jo9516650

文献信息

• Synthesis of All the Stereoisomers of 13,17-Dimethyl-1-tritriacontene and 13,17-Dimethyl-1-pentatriacontene, the Contact Sex Pheromone Components of the Female Tsetse Fly, Glossina austeni
  作者：Taichi Kimura、David A. Carlson、Kenji Mori

  DOI：10.1002/1099-0690(200109)2001:17<3385::aid-ejoc3385>3.0.co;2-p

  日期：2001.9

  All of the stereoisomers of 13,17-dimethyl-1-tritriacontene (1) and 13,17-dimethyl-1-pentatriacontene (2), the contact sex pheromone components of the female tsetse fly (Glossina austeni), were synthesized starting from the enantiomers of the protected syn- and anti-2,6-dimethylheptane-1,7-diol (3), which were prepared from the enantiomers of methyl 3-hydroxy-2-methylpropanoate (4) and methyl phenyl

  雌性采采蝇 (Glossina austeni) 的接触性信息素成分 13,17-二甲基-1-tritricontene (1) 和 13,17-二甲基-1-pentacontene (2) 的所有立体异构体都是从合成的受保护的顺-和反-2,6-二甲基庚烷-1,7-二醇 (3) 的对映体，由 3-羟基-2-甲基丙酸甲酯 (4) 和甲基苯砜 (5) 的对映体制备.
• 1,5-Acyclic stereoselection. The stereocontrolled synthesis of optically active vitamin E fourteen-carbon side chain alcohol
  作者：Gervais Bérubé、Pierre Deslongchamps

  DOI：10.1139/v84-267

  日期：1984.8.1

  The Diels–Alder product 3 was first transformed into the symmetrical nine-membered cyclic carbonate 8. Reaction of 8 with l-(−)-α-methylbenzylamine (12) yielded a mixture of optically active diastereoisomeric urethanes 9a (9, R = H, R′ = C₆H₅CHCH₃NHCO—) and 9b (9, R = C₆H₅CHCH₃NHCO—, R′ = H) which were separated and respectively converted into 11a and 11b. Compounds 11a and 11b were then transformed respectively into the optically active side chain alcohol 2 (R = H) of vitamine E (1).

  Diels-Alder产物3首先转化为对称的九元环碳酸酯8。8与l-(−)-α-甲基苄胺（12）反应生成了光学活性的二对映异构尿素衍生物9a（9，R = H，R′ = C6H5CHCH3NHCO—）和9b（9，R = C6H5CHCH3NHCO—，R′ = H），分离并分别转化为11a和11b。化合物11a和11b随后分别转化为维生素E（1）的光学活性侧链醇2（R = H）。
• Berube; Deslongchamps, Bulletin de la Societe Chimique de France, 1987, vol. No. 1, # 1, p. 103 - 115
  作者：Berube、Deslongchamps

  DOI：——

  日期：——
• Enzymatic Desymmetrization of <i>meso</i>-2,6-Dimethyl-1,7-heptanediol. Enantioselective Formal Synthesis of the Vitamin E Side Chain and the Insect Pheromone Tribolure
  作者：Robert Chênevert、Michel Desjardins

  DOI：10.1021/jo9516650

  日期：1996.1.1

  The chiral syn-1,5-dimethylalkyl subunit is found in many natural products with significant biological activities. Enzymatic esterification of meso-2,6-dimethyl-1,7-heptanediol with isopropenyl acetate in the presence of Pseudomonas cepacia lipase in organic medium provided the chiral nonracemic monoester in high enantiomeric excess (ee = 95%). This chiral building block was used in the formal syntheses of vitamin E side chain and the insect pheromone tribolure.