erythro-(2S,3R)-2-(N,N-dibenzylamino)-5-hexen-3-ol | 111060-74-3

• 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: erythro-(2S,3R)-2-(N,N-dibenzylamino)-5-hexen-3-ol
• 英文别名: (2S,3R)-2-(dibenzylamino)hex-5-en-3-ol
• CAS: 111060-74-3
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: WASYHJXAWKKGCR-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  erythro-(2S,3R)-2-(N,N-dibenzylamino)-5-hexen-3-ol 生成 5(S)-amino-4(R)-hydroxyhexene
  参考文献：
  名称：

  REETZ, MANFRED T.;DREWES, MARK W.;SCHMITZ, ALFRED, ANGEW. CHEM., 99,(1987) N 11, 1186-1188

  摘要：

  DOI：
• 作为产物：
  描述：

  L-丙氨酸,N,N-二(苯基甲基)-,苯基甲基酯 在 indium 、 ammonium chloride 作用下， 反应 6.08h， 生成 erythro-(2S,3R)-2-(N,N-dibenzylamino)-5-hexen-3-ol
  参考文献：
  名称：

  Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents

  摘要：

  The stereochemistry of the indium-promoted reaction of allyl bromide with alpha-thia (PhS and MeS), disubstituted alpha-amino (Bn2N, Me2N, isoindolyl), and protected alpha-amino aldehydes (Ac and Boc) in water has been evaluated. The reactions involving the sulfur derivatives are minimally diastereoselective, indicating that the allylindium reagent is not thiophilic. Chelation is not observed and pi-facial discrimination is achieved via Felkin-Ahn transition states under the steric control of the substituents. The Garner aldehyde is also anti-diastereoselective. Interestingly, N-acetylmannosamine is appreciably responsive to chelation control and is capable of generating 90% of the syn beta-amino alcohol when reacted in a 0.5 M NH4Cl solution. While the alpha-dibenzylamino substituent is too bulky to enter into complexation, the alpha-dimethylamino group is not and can lead to high levels (99%) of syn diastereomer. The size of other neighboring substituents does have an impact on pi-facial discrimination in these systems and can erode the stereoselectivity accordingly.

  DOI：

  10.1021/jo970274d

文献信息

• Enantiodivergent Biosynthesis of the Dimeric Sphingolipid Oceanapiside from the Marine Sponge <i>Oceanapia phillipensis</i>. Determination of Remote Stereochemistry
  作者：Gillian M. Nicholas、Tadeusz F. Molinski

  DOI：10.1021/ja994215o

  日期：2000.5.1

  determination of the local relative configuration at each of the termini of the long chain bis-aminolipid and also relates the absolute configuration of the two remote termini. Oceanapiside contains erythro and threo relative configurations at C1,2 and C26,27, respectively, but opposite absolute configurations at the amino substituted carbons C2 and C27 which implies an enantiodivergent biogenesis formally

  Oceanapiside 的绝对立体化学是一种具有四个立体中心的抗真菌 α,ω-双氨基羟基脂质，来自海洋海绵 Oceanapia phillipensis Dendy，1895，通过基于通用 CD 方法的开发和应用获得了 2S、3R、26R、27R双氨基醇过苯甲酰基衍生物中加性激子耦合的叠加。该方法允许同时确定长链双氨基脂的每个末端的局部相对构型，并且还涉及两个远程末端的绝对构型。Oceanapiside 分别在 C1,2 和 C26,27 处包含赤型和苏式相对构型，但在氨基取代的碳 C2 和 C27 处具有相反的绝对构型，这意味着从 d 和 l 氨基酸正式衍生的对映发散生物发生。
• Zinc-Mediated Allylation of <i>N</i>-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of <i>Anti</i>- and <i>Syn</i>-β-Amino Alcohols with Functionalized Allyl Groups
  作者：Stephen Hanessian、Haeil Park、Rui-Yang Yang

  DOI：10.1055/s-1997-804

  日期：1997.4

  Anti-β-amino alcohols with differently substituted allyl groups were obtained in high chemical yields and in good to excellent diastereoselectivities via Zn-mediated allylation of 2-(dibenzylamino)aldehydes in aqueous media. Swern oxidation, and reduction with NaBH4 gave enantiopure syn-β-amino alcohols in good yields.

  在水中通过锌介导的2-(二苄基氨基)醛的烯丙基化反应，以高化学产率和良好的至优异的非对映选择性获得了具有不同取代烯丙基的抗-β-氨基醇。通过Swern氧化和NaBH4还原，以良好产率得到了高对映纯度的顺-β-氨基醇。
• New organometallic approach to derivatives of α-substituted statines from N,N-dibenzylaminoaldehydes
  作者：Nicolas Le Carrer-Le Goff、Patrick Audin、Joëlle Paris、Bernard Cazes

  DOI：10.1016/s0040-4039(02)01401-6

  日期：2002.9

  alpha-Substituted statines derivatives were synthesized via the zinc-mediated allylation of N,N-dibenzyl alpha-aminoaldehydes followed by ozonolysis of the intermediate homoallylic alcohols. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Reetz, Manfred T.; Drewes, Mark W.; Schmitz, Alfred, Angewandte Chemie, 1987, vol. 99, # 11, p. 1186 - 1188
  作者：Reetz, Manfred T.、Drewes, Mark W.、Schmitz, Alfred

  DOI：——

  日期：——
• REETZ, MANFRED T., PURE AND APPL. CHEM., 60,(1988) N1, C. 1607-1614
  作者：REETZ, MANFRED T.

  DOI：——

  日期：——