(2R,3R,4S)-2-(Benzyloxy)-4-methyl-5-hexen-3-ol | 124377-76-0

• 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-(Benzyloxy)-4-methyl-5-hexen-3-ol
• 英文别名: (2R,3R,4S)-4-methyl-2-phenylmethoxyhex-5-en-3-ol
• CAS: 124377-76-0
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XNDKLMZGNVWKGI-OUCADQQQSA-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：

  (2R,3R,4S)-2-(Benzyloxy)-4-methyl-5-hexen-3-ol 在 氨 、 lithium 、 potassium hydride 作用下， 生成 tert-butyl((2R,3R,4S)-3-methoxy-4-methylhex-5-en-2-yloxy)dimethylsilane
  参考文献：
  名称：

  根瘤菌素的合成研究。二。到C的方法10 C 26亚基使用“衬底定向” allylstannane增补醛

  摘要：

  一个C的结构10 C 26的16-元大环内酯抗肿瘤根瘤菌素片段具有以有效的方式实现。该分子的中心部分已通过对映异构纯的形式，从（R）-乳酸的酯开始，通过重复的烯丙基甲磺酰化方法制备。经由二碘化sa改性的Julia偶联连接了根霉菌素的恶唑部分，以产生所需的全部E三烯。

  DOI：

  10.1016/0040-4039(96)00578-3
• 作为产物：
  描述：

  (R)-(+)-isobutyl O-benzyllactate 在 二异丁基氢化铝 、 magnesium bromide 作用下， 反应 0.33h， 生成 (2R,3R,4S)-2-(Benzyloxy)-4-methyl-5-hexen-3-ol
  参考文献：
  名称：

  根瘤菌素的合成研究。二。到C的方法10 C 26亚基使用“衬底定向” allylstannane增补醛

  摘要：

  一个C的结构10 C 26的16-元大环内酯抗肿瘤根瘤菌素片段具有以有效的方式实现。该分子的中心部分已通过对映异构纯的形式，从（R）-乳酸的酯开始，通过重复的烯丙基甲磺酰化方法制备。经由二碘化sa改性的Julia偶联连接了根霉菌素的恶唑部分，以产生所需的全部E三烯。

  DOI：

  10.1016/0040-4039(96)00578-3

文献信息

• Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to α-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems
  作者：Leo A. Paquette、Thomas M. Mitzel

  DOI：10.1021/jo9613489

  日期：1996.1.1

  The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted a-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti,syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and ''anti-Felkin'' transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.
• 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.
• Stereochemical aspects of the additions of anti-selective, crotyl organometallic reagents to .alpha.-alkoxy aldehydes
  作者：Stephen F. Martin、Wei Li

  DOI：10.1021/jo00287a032

  日期：1989.12
• MARTIN, STEPHEN F.;LI, WEI, J. ORG. CHEM., 54,(1989) N6, C. 6129-6133
  作者：MARTIN, STEPHEN F.、LI, WEI

  DOI：——

  日期：——
• BROWN, H. C.;BHAT, K. S.;RANDAD, K. S., J. ORG. CHEM., 52,(1987) N 16, 3701-3702
  作者：BROWN, H. C.、BHAT, K. S.、RANDAD, K. S.

  DOI：——

  日期：——