(4R,5R,E)-4,6-bis(benzyloxy)-5-hydroxyhex-2-enal | 137410-20-9

• 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: (4R,5R,E)-4,6-bis(benzyloxy)-5-hydroxyhex-2-enal
• 英文别名: (E,4R,5R)-5-hydroxy-4,6-bis(phenylmethoxy)hex-2-enal
• CAS: 137410-20-9
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: OQZYYYDXDCKYJE-CBHAQVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R,E)-4,6-bis(benzyloxy)-5-hydroxyhex-2-enal 在 titanium(IV) isopropylate 叔丁基过氧化氢 、 sodium tetrahydroborate 、 cerium(III) chloride 、 L-(+)-酒石酸二乙酯 、 柠檬酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 (2S,3S,4S,5R)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-D-galactitol
  参考文献：
  名称：

  An expedient route for the practical synthesis of pachastrissamine (jaspine B) starting from 3,4,6-tri-O-benzyl-d-galactal

  摘要：

  A practically efficient stereoselective synthesis of pachastrissamine (jaspine B) is described starting from 3,4,6-tri-O-benzyl-Dgalactal in eight steps and 11% overall yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.021
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 硫酸 、 mercury(II) sulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 (4R,5R,E)-4,6-bis(benzyloxy)-5-hydroxyhex-2-enal
  参考文献：
  名称：

  从d-半乳糖开始的立体选择性全合成Penaresidin A

  摘要：

  已经完成了Penaresidin A的立体选择性全合成，涉及Sharpless不对称环氧化，环氧化物的区域选择性开环，通过S N 2反应形成氮杂环丁烷，Jung方案和Julia - Kocienski烯烃化反应。该方法已经成功地证明了d-半乳糖在天然产物氮杂环丁烷核的构建中的合成效用。

  DOI：

  10.1016/j.tetlet.2013.10.095

文献信息

• Studies on epoxidation of enantiomerically pure 2,3-dideoxy hex-2-enitols: a convenient access to highly functionalized enantiomerically pure tetrahydrofuran derivatives
  作者：Ram Sagar、L. Vijaya Raghava Reddy、Arun K. Shaw

  DOI：10.1016/j.tetasy.2006.04.022

  日期：2006.4

  8–14 derived from their respective glycals with Sharpless, m-CPBA and Camp’s reagents was carried out in order to obtain 2,3-epoxy alcohols keeping in view the versatility of these synthons in synthetic chemistry for the preparation of various molecules of biological importance by suitable chemical transformations. During the course of this study, the Sharpless asymmetric epoxidation reaction was found

  上对映体纯的烯丙醇的环氧化的详细比较研究8 - 14从与夏普勒斯，其各自衍生烯糖米-CPBA和坎普的试剂是为了获得2,3-环氧醇鉴于保持这些合成子的通用性进行在合成化学中用于通过合适的化学转化制备具有生物学重要性的各种分子。在该研究过程中，由于其温和的反应条件，Sharpsless不对称环氧化反应被发现是一种空前的替代方法，用于合成高度官能化的对映体纯的四氢呋喃衍生物。还研究了它们形成的详细机理。
• Metal free synthesis of 2,3-dideoxy-α, β-unsaturated carbohydrate enals (Perlin aldehydes)
  作者：Kavita Singh、Sourav Sagar Behera、Rajdeep Tyagi、Ghanshyam Tiwari、Ram Sagar

  DOI：10.1016/j.carres.2023.108890

  日期：2023.9

  A metal free synthesis of enantiopure 2,3-dideoxy-α, β-unsaturated carbohydrate enals (Perlin aldehydes), in CH3CN-0.02 N H2SO4 in water (1:1, v/v) with 0.5 equivalent additives (4-hydroxy-6-methyl-2-pyrone or 4-amino coumarin), has been reported. This efficient protocol works well for the acetylated glycals (glucal, galactal and arabinal) and afforded Perlin aldehydes and hemiacetals in acceptable

  无金属合成对映体纯 2,3-二脱氧-α, β-不饱和碳水化合物烯醛（Perlin 醛），在 CH 3 CN-0.02 N H 2 SO 4水溶液（1:1，v/v）中使用 0.5 当量添加剂（ 4-羟基-6-甲基-2-吡喃酮或4-氨基香豆素）已被报道。这种高效的方案适用于乙酰化糖醛（葡萄糖、半乳糖和阿拉伯糖），并以可接受的良好产率提供柏林醛和半缩醛。然而，在类似的反应条件下，苄基化的糖醛分别提供柏林醛、半缩醛和2-脱氧衍生物。当从反应混合物中去除添加剂时，产物收率显着降低，表明它们构成了该方法的重要组成部分。此外，使用0.02 NH 2 SO 4的水：乙腈（1:1，v/v）溶剂系统对于柏林醛的形成至关重要。在中性反应条件（CH 3 CN:H 2 O，1:1，v/v）下与添加剂进行类似的反应，得到半缩醛作为主要产物。该方法是一种无金属的柏林醛合成方法，因此在生物活性药物分子的制备中具有额外的好处，其中金属毒性是主要问题。
• InCl3–CH3CN–H2O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars
  作者：Paramathevar Nagaraj、Muthupandian Ganesan、Namakkal G. Ramesh

  DOI：10.1016/j.tet.2010.11.050

  日期：2011.1

  InCl3-CH3CN-H2O has been found to be an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. While acetylated glycals afforded the Perlin aldehydes directly with InCl3 and water, benzylated glycals on the other hand provided the hemiacetals under identical condition. The methodology reports a non-mercurial approach to Perlin aldehydes. Noteworthy is that this reaction is more facile as well as highly selective with glycals possessing a hydroxyl as a leaving group than with a benzyloxy group. Extension of this reaction to 2-C-hydroxymethyl glycals resulted in the formation of the corresponding hemiacetals, which were further transformed in to unsaturated azasugars with an exo-methylene group at C-2 position. Glycosidase inhibition studies reveal that these compounds display selectivity in inhibiting glucosidases rather than galactosidases. (C) 2010 Elsevier Ltd. All rights reserved.
• An efficient synthesis of 2,3-dideoxy-α,β-unsaturated carbohydrate enals by mixed Lewis acid (HfCl4 and ZnI2) catalyzed hydration of glycals
  作者：Mohammad Saquib、Ram Sagar、Arun K. Shaw

  DOI：10.1016/j.carres.2006.02.031

  日期：2006.6

  A new, efficient method has been developed for converting acyl-, arylalkyl- and alkyl-protected glycals into corresponding 2,3 -dideoxy-alpha, beta-unsaturated carbohydrate enals utilizing the in situ generated push-pull effect resulting from the synergistic combination of HfCl4 and ZnI2 in catalytic amounts. This new procedure eliminates the use of highly toxic Hg2+ ions and acidic conditions (0.01-0.02 N H2SO4), besides radically shortening the reaction time. (c) 2006 Elsevier Ltd. All rights reserved.
• α-Glycosphingolipids via Chelation-Induced Anomerization of <i>O</i>- and <i>S</i>-Glucuronic and Galacturonic Acid Derivatives
  作者：Wayne Pilgrim、Paul V. Murphy

  DOI：10.1021/ol802915h

  日期：2009.2.19

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.