(2R,3R,4S)-2-(benzyloxymethoxy)-4-methylhex-5-en-3-ol | 159572-28-8

• 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: (2R,3R,4S)-2-(benzyloxymethoxy)-4-methylhex-5-en-3-ol
• 英文别名: (2R,3R,4S)-4-methyl-2-(phenylmethoxymethoxy)hex-5-en-3-ol
• CAS: 159572-28-8
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: HESPIEABRTVDMF-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-(benzyloxymethoxy)-4-methylhex-5-en-3-ol 、 碘甲烷 在 potassium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.5h， 以92%的产率得到(2R,3R,4S)-2-(benzyloxymethoxy)-3-methoxy-4-methylhex-5-ene
  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：

  三丁基(1-甲基烯丙基)锡 、 (R)-2-((benzyloxy)methoxy)propanal 在 magnesium bromide ethyl etherate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以1.13 g的产率得到(2R,3R,4S)-2-(benzyloxymethoxy)-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

• Chelation controlled diastereofacial selectivity in crotyltri--butylstannane additions to α-alkoxyaldehydes
  作者：Gary E. Keck、Eugene P. Boden

  DOI：10.1016/s0040-4039(01)90065-6

  日期：1984.1

  Lewis acid mediated additions of crotyltri-n-butylstannane to chiral α-alkoxyaldehydes generally show excellent (⩾99:1) diastereofacial selectivity; proper choice of lewis acid is crucial for controlling erythro/threo selectivity in the bond formation.

  路易斯酸介导的巴豆基三正丁基锡烷向手性α-烷氧基醛中的加成通常表现出极好的（⩾99：1）非对映选择性。正确选择路易斯酸对于控制键形成中的赤/苏选择性至关重要。
• Effects of Olefin Geometry on the Stereochemistry of Lewis Acid Mediated Additions of Crotylstannanes to Aldehydes
  作者：Gary E. Keck、Kenneth A. Savin、Erik N. K. Cressman、Duane E. Abbott

  DOI：10.1021/jo00104a054

  日期：1994.12

  The role of the double bond geometry (E/Z stereochemistry) in reactions of crotylstannanes with aldehydes has been examined for representative ''simple'', alpha-alkoxy, and beta-alkoxy aldehydes. For the reaction of crotylstannane with simple achiral aliphatic, aromatic, or alpha,beta unsaturated aldehydes mediated by BF3.Et(2)O, use of the E crotylstannane gives much enhanced syn selectivity over that obtained with Z (e.g., 43:1 vs 4:1 with benzaldehyde). A synclinal transition state in which the CH(2)SnBu(3) group is gauche to oxygen is proposed to explain these results. For alpha-alkoxy aldehydes, use of the E stannane with MgBr2 gives the highest syn selectivity, while the Z stannane gives slightly better stereoselectivity with beta-alkoxy substrates. In contrast, the use of TiCl4 gives anti products preferentially from the E stannane and either alpha or beta-alkoxy substrates.