(2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol | 109333-88-2

• 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,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol
• 英文别名: (2S,3S,4S)-2-(benzyloxy)-4-methyl-5-hexen-3-ol；(2S,3S,4S)-4-methyl-2-phenylmethoxyhex-5-en-3-ol
• CAS: 109333-88-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XNDKLMZGNVWKGI-OBJOEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol 、 2-吡啶基甲基甲酸酯 在 十二羰基三钌 、 N-甲基吗啉氧化物 作用下， 反应 18.0h， 以59%的产率得到(5S,6S)-6-((S)-1-(benzyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of GEX1A

  摘要：

  An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 (1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.

  DOI：

  10.1021/ol800902g
• 作为产物：
  描述：

  反-2-丁烯 、 (S)-2-苄氧基丙醛 在 正丁基锂 、 potassium tert-butylate 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以1.36 g的产率得到(2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol
  参考文献：
  名称：

  Total Synthesis of GEX1A

  摘要：

  An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 (1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.

  DOI：

  10.1021/ol800902g

文献信息

• Anomalous threo-diastereoselectivity in allylic silane- or stannane–aldehyde condensation reactions: new interpretation of the antiperiplanar vs. synclinal problem on the transition-state conformations
  作者：Koichi Mikami、Kazuya Kawamoto、Teck-Peng Loh、Takeshi Nakai

  DOI：10.1039/c39900001161

  日期：——

  Unusual threo-diastereoselectivity has been observed in the intermolecular reactions of β-substituted crotyl-silane or-stannane with 2-benzyloxypropanal under chelation conditions, which implies preference for the synclinal over the antiperiplanar transition state.

  在螯合条件下，β-取代的巴豆基硅烷或锡烷与2-苄氧基丙醛的分子间反应中观察到了不寻常的苏-非对映选择性，这表明对苯二酚的偏爱于反平面的过渡态。
• Chiral synthesis via organoboranes. 21. Allyl- and crotylboration of .alpha.-chiral aldehydes with diisopinocampheylboron as the chiral auxiliary
  作者：Herbert C. Brown、Krishna S. Bhat、Ramnarayan S. Randad

  DOI：10.1021/jo00268a017

  日期：1989.3
• Allylcopper Intermediates with N-Heterocyclic Carbene Ligands: Synthesis, Structure, and Catalysis
  作者：Vincenzo Russo、Jessica R. Herron、Zachary T. Ball

  DOI：10.1021/ol902458v

  日期：2010.1.15

  Allylcopper intermediates with N-heterocyclic carbene ligands are synthesized by transmetalation of allylsiloxane reagents, and the crystal structures of allylcopper compounds are reported. The allylcopper transmetalation is utilized for catalytic aldehyde allylation, which is found to be facilitated by a trifluorosilane co-catalyst.
• BROWN, HERBERT C.;BHAT, KRISHNA S.;RANDAD, RAMNARAYAN S., J. ORG. CHEM., 54,(1989) N, C. 1570-1576
  作者：BROWN, HERBERT C.、BHAT, KRISHNA S.、RANDAD, RAMNARAYAN S.

  DOI：——

  日期：——
• Total Synthesis of GEX1A
  作者：Timothy J. Murray、Craig J. Forsyth

  DOI：10.1021/ol800902g

  日期：2008.8.21

  An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 (1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.