(2RS,3SR)-hex-5-ene-1,2,3-triol | 79364-36-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2RS,3SR)-hex-5-ene-1,2,3-triol
• 英文别名: (+/-)-erythro-hex-5-ene-1,2,3-triol；(+/-)-erythro-Hex-5-en-1,2,3-triol；opt. inakt. Hexen-(5)-triol-(1,2,3)；Hexen-(5)-triol-(1,2,3)；(2S,3R)-hex-5-ene-1,2,3-triol
• CAS: 79364-36-6；89534-51-0；99096-92-1；99146-85-7；99146-86-8
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: LOUUJHLYXOLVKW-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-hex-5-ene-1,2,3-triol 在 甲酸 、 双氧水 作用下， 生成 1,2,3,5,6-hexanepentaol
  参考文献：
  名称：

  Herault,V., Bulletin de la Societe Chimique de France, 1963, p. 2105 - 2113

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2,2-dimethyl[1,3]dioxolan-4-yl)but-3-en-1-ol 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (2RS,3SR)-hex-5-ene-1,2,3-triol
  参考文献：
  名称：

  （+）-甘氨酸酸A及其类似物的全合成及生物学评价

  摘要：

  在这项研究中，我们详细报告了冈比亚酸A（一种有效的抗真菌多环醚代谢物）的首次总合成和完整的立体结构。A / B环外环烯醇醚32是通过B环乙烯基碘18与烷基硼酸酯33的Suzuki-Miyaura偶联反应制备的，随后通过使用非对映选择性溴醚化作为关键转化来封闭A环。Suzuki-Miyaura将32与乙酸酯衍生的烯醇磷酸酯49偶联，然后将衍生的二烯进行开环易位，产生了D环。随后通过混合硫代缩醛化作用封闭C环，完成了A / BCD环片段的合成8。A / BCD和F'GHIJ环片段（即8和9）是通过Suzuki-Miyaura偶合组装的。通过利用七元F'环的内在构象特性，对C25立体生成中心进行了阐述。F'环被氧化裂解后，E环形成为环状混合硫缩醛（即70），然后使用糖基化化学方法进行立体选择性烯丙基化。由此获得的二烯3的闭环复分解反应关闭了F环并完成了多环醚骨架。最后，在存在CeCl 3的情况下

  DOI：

  10.1002/chem.201204303

文献信息

• Molybdenum-Catalyzed Hydroxyl-Directed <i>Anti</i>-Dihydroxylation of Allylic and Homoallylic Alcohols
  作者：Pei Fan、Shixia Su、Chuan Wang

  DOI：10.1021/acscatal.8b01449

  日期：2018.8.3

  A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO2(acac)2, an array of hydroxylated dienes were successfully converted into various

  已经开发了烯丙基和均烯丙基醇的催化羟基定向的抗二羟基化。这种操作简单的方法已成功地应用于含有至少一个远端烯烃单元的烯丙基醇的直接抗单二羟基化反应。在市售MoO 2（acac）2的催化下，使用过氧化氢作为环境良性氧化剂，在有氧条件下，特别是在完全区域选择性和氢键作用下，成功地将一系列羟基化的二烯成功转化为各种1,2,3-三醇。大多数情况下采用非对映特异性途径。
• Gallium-mediated allylation of carbonyl compounds in water
  作者：Zhiyong Wang、Shizhen Yuan、Chao-Jun Li

  DOI：10.1016/s0040-4039(02)00995-4

  日期：2002.7

  Ga-mediated allylation of aldehydes or ketones in distilled or tap water generated the corresponding homoallyl alcohols in high yields without the assistance of either acidic media or sonication.

  镓介导的蒸馏水或自来水中醛或酮的烯丙基化反应可在不借助酸性介质或超声处理的情况下，以高收率生成相应的均烯丙基醇。
• Synthesis of beta-L-2-Deoxy nucleosides
  申请人：Novartis AG

  公开号：EP2157095A2

  公开（公告）日：2010-02-24

  An improved process for the preparation of 2'-modified nucleosides and 2'-deoxynucleosides, such as, β-L-2'-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2'-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2' anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2'-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2'-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2'-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  本发明提供了一种改进的方法，用于制备2'-修饰核苷和2'-去氧核苷，例如β-L-2'-去氧胸腺嘧啶（LdT）。特别是，改进的方法针对合成一种2'-去氧核苷，该方法可以利用不同的起始材料，但是通过氯代糖中间体或2,2'无水-1-呋喃基-核碱中间体进行。当使用2,2'-无水-1-呋喃基碱中间体时，采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），引起分子内位移反应并形成所需的核苷产物，产率良好。本发明的另一种替代方法利用无隔离剂的2,2'-无水-1-呋喃基碱中间体，以获得良好的2'-去氧核苷收率。根据本发明制备的化合物可以用作制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction
  作者：Shun Kitahata、Akira Katsuyama、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.0c00665

  日期：2020.4.3

  A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the alpha-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.
• Synthesis of sn-1 functionalized phospholipids as substrates for secretory phospholipase A2
  作者：Lars Linderoth、Günther H. Peters、Kent Jørgensen、Robert Madsen、Thomas L. Andresen

  DOI：10.1016/j.chemphyslip.2006.12.006

  日期：2007.3

  Secretory phospholipase A2 (sPLA2) represents a family of small water-soluble enzymes that catalyze the hydrolysis of phospholipids in the sn-2 position liberating free fatty acids and lysophospholipids. Herein we report the synthesis of two new phospholipids (1 and 2) with bulky allyl-substituents attached to the sn-1 position of the glycerol backbone. The synthesis of phospholipids 1 and 2 is based upon the construction of a key aldehyde intermediate 3 which locks the stereochemistry in the sn-2 position of the final phospholipids. The aldehyde functionality serves as the site for insertion of the allyl-substituents by a zinc mediated allylation. Small unilamellar liposomes composed of phospholipids 1 and 2 were subjected to sPLA2 activity measurements. Our results show that only phospholipid 1 is hydrolyzed by the enzyme. Molecular dynamics simulations revealed that the lack of hydrolysis of phospholipid 2 is due to steric hindrance caused by the bulky side chain of the substrate allowing only limited access of water molecules to the active site.