(2S,3R,4S)-2,3-epoxyhept-6-en-4-ol | 81076-06-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S)-2,3-epoxyhept-6-en-4-ol
• 英文别名: (4S,5S,6S)-5,6-epoxyhept-1-en-4-ol；(2S,3R,4S)-(-)-2,3-Epoxy-6-hepten-4-ol；(1S)-1-[(2S,3S)-3-methyloxiran-2-yl]but-3-en-1-ol
• CAS: 81076-06-4
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: HWQJBKYWCZLOSU-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-2,3-epoxyhept-6-en-4-ol 在 咪唑 、 chromium(VI) oxide 、 盐酸 、 三乙基硅烷 、 三乙基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 臭氧 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 甲苯 为溶剂， 生成 (S)-2-甲基四氢吡喃-4-酮
  参考文献：
  名称：

  4-甲氧基-2-甲基四氢吡喃：手性白三烯生物合成抑制剂，与ICI D2138有关，显示对映选择性。

  摘要：

  DOI：

  10.1021/jm00054a016
• 作为产物：
  描述：

  (5E)-hepta-1,5-dien-4-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 二甲基硫 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 作用下， 生成 (2S,3R,4S)-2,3-epoxyhept-6-en-4-ol
  参考文献：
  名称：

  swinholide A的总合成。第1部分：C19-C32段的立体控制合成

  摘要：

  从（±）-16分15步（产率为8％，产率为82％ds）制备了Swinholide A的C 19 -C 32链段10。关键步骤包括（i）Sharpless环氧化16 → 17，（ii）乙缩醛烯丙基化15 → 23，（iii）抗羟醛加成13 + 14→12和（iv）烯烃硼氢化30→31。swinholides是一系列复杂的聚酮大环氧化物，对多种人类肿瘤细胞系均显示出强大的细胞毒性。1,2从海洋海绵中分离出的Swinholide A1985年，Carmely和Kashman首次报道了Theonella swinhoei作为抗真菌剂。1使用NMR方法和化学方法

  DOI：

  10.1016/0040-4020(95)00546-k

文献信息

• Stereoselective synthesis of (+)-cryptocarya diacetate by an iterative Prins cyclisation and reductive cleavage sequence
  作者：J.S. Yadav、P. Purushothama Rao、M. Sridhar Reddy、N. Venkateswar Rao、A.R. Prasad

  DOI：10.1016/j.tetlet.2006.12.068

  日期：2007.2

  A highly stereoselective synthesis of (+)-cryptocarya diacetate is achieved through our recently developed strategy for the construction of 1,3-diols via Prins cyclisation. The route relies mainly on the reductive cleavage of allylic ethers, ozonolysis and Wittig olefination along with Prins cyclisation.

  通过我们最近开发的通过Prins环化反应构建1,3-二醇的策略，可以实现（+）-隐球菌双乙酸酯的高度立体选择性合成。该路线主要依赖于烯丙基醚的还原裂解，臭氧分解和维蒂希烯化以及普林斯环化反应。
• Towards the Synthesis of Aureolic Acid Analogue Conjugates: Synthesis and Glycosidation Reactions of 3-O-Acetyl-4-azido-2,4,6-trideoxy-L-glucopyranose Derivatives
  作者：W. R. Roush、R. A. James

  DOI：10.1071/ch01199

  日期：——

  A stereoselective synthesis of 3-O-acetyl-4-azido-glucopyranose (6) is described. The derived anomeric acetate (13), and especially the thioglycoside (14), are demonstrated to be good donors for synthesis of α-glycosides of (6). Donor (14) was used in the synthesis of trisaccharide (21), which is targeted for use in the synthesis of the aureolic acid trisaccharide conjugate analogue (5).

  描述了 3-O-乙酰基-4-叠氮基-吡喃葡萄糖 (6) 的立体选择性合成。衍生的异头乙酸酯 (13)，尤其是硫代糖苷 (14)，被证明是合成 (6) 的 α-糖苷的良好供体。供体 (14) 用于三糖 (21) 的合成，该三糖 (21) 的目标是用于合成金黄酸三糖缀合物类似物 (5)。
• Carbohydrate-like chiral synthons: Synthesis of the N-trifluoroacetyl derivatives of 4-amino-2,4,6-trideoxy-l-lyxo-, -l-arabino, and -l-ribo-hexose from the (2S,3R)-2,3-diol formed from cinnamaldehyde in fermenting baker's yeast
  作者：Giovanni Fronza、Claudio Fuganti、Piero Grasselli、Giuseppe Pedrocchi-Fantoni

  DOI：10.1016/0008-6215(85)85190-9

  日期：1985.2

  formed from cinnamaldehyde in fermenting baker's yeast, affords, with diallyl-zinc, the C7, carbohydrate-like, noncarbohydrate-derived adduct (2S,3R,4R)-2,3-isopropylidenedioxy-4-hydroxyhept-6-ene (9). This material is a stereochemically defined, functionalised, chiral synthon which is useful in the synthesis of enantiomerically pure products. The synthesis of the N-trifluoroacetyl derivatives of 4-amino-2

  摘要（2S，3S）-2,3-异丙基二烯二氧基丁醛，是通过将肉桂醛形成的O-异丙基亚甲基化的（2S，3R）-2,3-二醇在面包师酵母中进行臭氧分解而制得的，它与二烯丙基锌一起提供C7，碳水化合物样，非碳水化合物衍生的加合物（2S，3R，4R）-2,3-异丙基二烯二氧基-4-羟基庚-6-烯（9）。该物质是立体化学定义的，官能化的手性合成子，可用于合成对映体纯的产物。据报道，由9合成了4-氨基-2,4,6-三苯氧基-1-lyxo（21），-1-阿拉伯糖（22）和-l-核糖己糖（23）的N-三氟乙酰基衍生物。 。合成中的关键中间体是异构的环氧醇（2S，3S，4S）-3,4-环氧庚烷6-烯-2-醇，（2S，3R，4S）-2,3-环氧庚烷-6-烯- 4-ol和（2S，3R，4R）-2,3-epoxyhept-6-en-4-ol。
• Heterocycles with inhibitory activity of 5-lipoxygenase
  申请人：ZENECA LIMITED

  公开号：EP0385662A2

  公开（公告）日：1990-09-05

  The invention concerns a heterocycle of the formula I wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms; A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene; X is oxy, thio, sulphinyl, sulphonyl or imino; Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms; R¹ is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; and R² and R³ together form a group of the formula -A²-X²-A³- which, together with the carbon atom to which A² and A³ are attached, defines a ring having 4 to 7 ring atoms, wherein A² and A³, which may be the same or different, each is (1-4C)alkylene and X² is oxy, thio, sulphinyl, sulphonyl or imino; or a pharmaceutically-acceptable salt thereof. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.

  本发明涉及式 I 的杂环 其中 Q 是含有一个或两个氮原子的任选取代的 6 元单环或 10 元双环杂环分子； A是(1-6C)亚烷基、(3-6C)烯基、(3-6C)炔基或环(3-6C)亚烷基； X 是氧基、硫代、亚砜基、磺酰基或亚氨基； Ar 是亚苯基，可任选带有一个或两个取代基，或者 Ar 是任选被取代的含有最多三个氮原子的 6 元杂环分子； R¹是氢、(1-6C)烷基、(3-6C)烯基、(3-6C)炔基、氰基-(1-4C)烷基或(2-4C)烷酰基，或任选取代的苯甲酰基； 与 R² 和 R³ 一起形成式 -A²-X²-A³- 的基团，该基团与 A² 和 A³ 所连接的碳原子一起定义了一个具有 4 至 7 个环原子的环，其中 A² 和 A³ 可以相同或不同，各自为 (1-4C)烷基，X² 为氧基、硫基、亚砜基、磺酰基或亚氨基； 或其药学上可接受的盐。 本发明的化合物是 5-脂氧合酶的抑制剂。
• A tellurium transposition route to allylic alcohols: overcoming some limitations of the Sharpless-Katsuki asymmetric epoxidation
  作者：Donald C. Dittmer、Robert P. Discordia、Yanzhi Zhang、Christopher K. Murphy、Archana Kumar、Aurora S. Pepito、Yuesheng Wang

  DOI：10.1021/jo00055a029

  日期：1993.1

  Good yields of enantiomeric allylic alcohols can be obtained in high enantiomeric excess (ee) by combining the Sharpless-Katsuki asymmetric epoxidation process (SAE) with tellurium chemistry. The advantages of the tellurium process are as follows: (1) the 50% yield limitation on the allylic alcohol in the Sharpless kinetic resolution (SKR) can be overcome; (2) allylic tertiary alcohols which are unsatisfactory substrates in the SKR can be obtained in high optical purity; (3) optically active secondary allylic alcohols with tertiary alkyl substituents (e.g. tert-butyl) at C-1 can be obtained in high ee; (4) optically active sterically congested cis secondary alcohols can be obtained in high ee; and (5) the nuisance of the slow SAE of some vinyl carbinols can be avoided. The key step in the reaction sequence is either a stereospecific 1,3-trans position of double bond and alcohol functionalities or an inversion of the alcohol configuration with concomitant deoxygenation of the epoxide function in epoxy alcohols. Trans secondary allylic alcohols can be converted to cis secondary allylic alcohols by way of erythro epoxy alcohols (glycidols); threo glycidyl derivatives are converted to trans secondary allylic alcohols. These transformations are accomplished by the action of telluride ion, generated in situ from the element, on a glycidyl sulfonate ester. Reduction of elemental Te is conveniently done with rongalite (HOCH2SO2Na) in an aqueous medium. This method is satisfactory when Te2- is required to attack a primary carbon site of a glycidyl sulfonate. In cases where Te2- is required to attack a secondary carbon site, reduction of the tellurium must be done with NaBH4 or LiEt3BH. Elemental tellurium is precipitated during the course of the reactions and can be recovered and reused.