(2R,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene | 116444-15-6

• 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,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene
• 英文别名: (2R,3S)-1,3-bis(benzyloxy)-hex-5-en-2-ol；(2R,3S)-1,3-bis(benzyloxy)hex-5-en-2-ol；(2R,3S)-1,3-bis(phenylmethoxy)hex-5-en-2-ol
• CAS: 116444-15-6
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: NXGBFLBVFSUYOK-UXHICEINSA-N

物化性质

• 沸点：
  448.7±45.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 6.83h， 生成 (4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-tetrahydro-furan-2-carbaldehyde
  参考文献：
  名称：

  A new synthetic route to oxazole and pyrrole 2-deoxy-C-ribosides

  摘要：

  The synthesis of oxazole and pyrrole 3-carbethoxy/3-arylsulfonyl D and L-2-deoxyribosides by TosMIC addition/cyclization on D and L-2-deoxyribo-1-carboxaldehyde and unsaturated esters in moderate to good yields is reported. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.06.110
• 作为产物：
  描述：

  1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 (2R,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene
  参考文献：
  名称：

  Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

  摘要：

  Two new [named xylapyrrosides A (1) and B (2)1 along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the Et0H extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A(1) (1a), A(2) (1b) and B-1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.020

文献信息

• ‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent
  作者：Pintu Das、Somireddy Kundooru、Arun K. Shaw

  DOI：10.1039/c5ra27342k

  日期：——

  overall yield of 33%) and unnatural antineoplastic and antipsoriatic drug safingol 17 (with an overall yield of 38%) starting from chirons 3,4,6-tri-O-benzyl-D-galactal and 3,4,6-tri-O-benzyl-D-glucal respectively have been demonstrated. Mitsunobu reaction and late stage olefin cross metathesis are utilized as important steps in order to complete the total synthesis of these sphingoid molecules.

  鞘氨醇碱，天然生物活性神经酰胺神经鞘氨醇1（总产率为33％）以及非天然抗肿瘤药和抗银屑病药物沙芬醇17（总产率为38％）的高度立体选择性全部合成，始于chirons 3,4,6-tri- ø苄基d -galactal和3,4,6-三- ö苄基d -glucal分别已被证实。Mitsunobu反应和后期烯烃交叉复分解被用作重要步骤，以完成这些类鞘氨醇分子的总合成。
• Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using Mitsunobu reaction
  作者：Nafizal Hossain、Jef Rozenski、Erik De Clercq、Piet Herdewijn

  DOI：10.1016/0040-4020(96)00818-6

  日期：1996.10

  Starting from protected hexenetriol, acyclic analogues of the 1,5-anhydrohexitol nucleosides were synthesized. The reaction sequence involved a stereoselective Sharpless dihydroxylation and a Mitsunobu-type alkylation of the nucleoside bases. The compounds did not show antiviral activity.

  从受保护的己三醇开始，合成了1，5-脱水己糖醇核苷的无环类似物。反应序列涉及核苷碱基的立体选择性Sharpless二羟基化和Mitsunobu型烷基化。该化合物没有显示抗病毒活性。
• A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose
  作者：Olaf R. Ludek、Victor E. Marquez

  DOI：10.1016/j.tet.2009.08.035

  日期：2009.10

  An enantioselective synthesis of suitably protected (1R,2S,4S,5S)-4-amino-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol, a key starting material for the synthesis of conformationally locked carbocyclic nucleosides, including the antiviral active North-methanocarbathymidine, is reported. Starting from 2-deoxyribose the target Boc-protected amine was prepared in 33% overall yield under conditions that are

  适当保护的 (1 R ,2 S ,4 S ,5 S )-4-氨基-1-(羟甲基)双环[3.1.0]己-2-醇的对映选择性合成，这是构象合成的关键原料据报道，锁定碳环核苷，包括具有抗病毒活性的 North-methanocarbathymidine。从 2-脱氧核糖开始，在比以前的方法更生态友好的条件下，以 33% 的总收率制备了目标 Boc 保护的胺。
• Total Synthesis and Stereochemical Revision of Acortatarins A and B
  作者：Gangarajula Sudhakar、Vilas D. Kadam、Shruthi Bayya、Gavinolla Pranitha、Bharatam Jagadeesh

  DOI：10.1021/ol202121k

  日期：2011.10.21

  A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole

  通过使用容易获得的d-糖描述了第一步的全合成的角蛋白A，B和对映体结构的对映体。这种聚合的总合成揭示了对阿考塔林A的绝对构型的修订和对阿考塔林B的结构的修订。涉及的关键步骤是用去质子化的2，5-二取代的吡咯进行的区域选择性环氧化物的开环和螺缩酮化。
• Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-<scp>d</scp>-ribopyranose ring system donors
  作者：Omar Boutureira、M. Isabel Matheu、Yolanda Díaz、Sergio Castillón

  DOI：10.1039/c4ra01668h

  日期：——

  units are important ring systems found in nature. Herein, we develop a metal-mediated strategy to form this important scaffold featuring a cross-metathesis reaction of the corresponding sugar-derived hydroxyalkene with electron-rich phenyl vinyl sulfide using commercially available ruthenium-catalysts under microwave irradiation as a key step. The final 2,3-dideoxyhexopyranose ring is generated in a

  2,3-二脱氧-D-核糖吡喃糖单元是自然界中重要的环系统。在本文中，我们开发了一种金属介导的策略来形成这种重要的支架，该支架具有相应的糖衍生的羟基烯烃与富电子的苯基乙烯基硫化物的交叉复分解反应，这是使用可商购的钌催化剂在微波辐射下进行的关键步骤。最终2,3- dideoxyhexopyranose环的确定在6-单个步骤中产生内切电环化。