(2S,6S)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptanol | 92934-89-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,6S)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptanol
• 英文别名: (2S,6R)-7-tert-butyldimethylsilyloxy-2,6-dimethyl-1-heptanol；(2S,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylheptan-1-ol
• CAS: 92934-89-9
• 化学式: C₁₅H₃₄O₂Si
• 分子量: 274.519
• InChiKey: OVRWHFIPANMEHY-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,6S)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptanol 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.75h， 生成 (2S,6R)-2,6-dimethyl-1-<(2'-methoxyethoxy)methoxy>-7-heptyl p-toluenesulfonate
  参考文献：
  名称：

  Acyclic stereoselection. Part 42. 1,4- and 1,5-Stereoselection by sequential aldol addition to a .alpha.,.beta.-unsaturated aldehydes followed by Claisen rearrangement. Application to total synthesis of the vitamin E side chain and the archaebacterial C40 diol

  摘要：

  DOI：

  10.1021/jo00244a017
• 作为产物：
  描述：

  2,6-dimethyl-1,7-heptanediol 在 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 55.0h， 生成 (2S,6S)-7-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1-heptanol
  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）。
• Acyclic stereoselection. 15. Sequential aldol-claisen as a method for 1,5-stereoselection. Total synthesis of the vitamin-E side chain
  作者：Clayton H. Heathcock、Esa T. Jarvi

  DOI：10.1016/s0040-4039(00)88423-3

  日期：1982.1

  Alcohol1, the side chain of α-tocopherol, has been synthesized in a stereoselective route involving an aldol condensation-Claisen rearrangement sequence. The synthesis require 11 steps and produces1in 17% overall yield. A complementary sequence employing reagent14provides isomer18.

  醇1，α生育酚的侧链，已经在涉及羟醛缩合-Claisen重排顺序的立体选择性路线被合成。合成需要11个步骤，并产生1在17％的总收率。甲互补序列使用试剂14提供异构体18。
• Total synthesis of a slightly unnatural product. Confirmation of the stereostructure of the archaebacterial C40 diol by synthesis of a stereoisomer
  作者：Clayton H. Heathcock、Peggy A. Radel

  DOI：10.1021/jo00372a051

  日期：1986.10
• Berube; Deslongchamps, Bulletin de la Societe Chimique de France, 1987, vol. No. 1, # 1, p. 103 - 115
  作者：Berube、Deslongchamps

  DOI：——

  日期：——