(2R,3S,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol | 24716-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,3S,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol
• 英文别名: 2-epi-jaspine B；2-epi-pachastrissamine；2-Epi jaspine B；(2R,3S,4S)-4-amino-2-tetradecyloxolan-3-ol
• CAS: 24716-56-1
• 化学式: C₁₈H₃₇NO₂
• 分子量: 299.497
• InChiKey: FBQCDJRSCUVUFL-KSZLIROESA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  422.9±45.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3S,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以81%的产率得到2-acetamido-3-O-acetyl-1,4-anhydro-(2S,3S,4R)-1,3,4-octadecanetriol
  参考文献：
  名称：

  的不对称合成Ñ，ø，ö，ö四-乙酰D-来苏-phytosphingosine，jaspine B（pachastrissamine）及其C（2）差向异构体

  摘要：

  （S）-N-苄基-N-（α-甲基苄基）酰胺锂的高非对映选择性共轭加成至γ-甲硅烷氧基-α，β-不饱和酯并用（+）-（樟脑磺酰基）恶唑烷原位烯醇氧化被用作不对称合成中的关键步骤ñ，ø，ö，ö四-乙酰D-来苏-phytosphingosine，jaspine B（pachastrissamine）及其C（2）差向异构体。

  DOI：

  10.1016/j.tetasy.2007.10.026
• 作为产物：
  描述：

  1-十四烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 反应 30.25h， 生成 (2R,3S,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Pachastrissamine（Jaspine B）及其非对映体的不对称合成经由η 3 π-烯丙基中间体

  摘要：

  合成以下物质的捷径 Pachastrissamine （茉莉花B），脱水鞘氨醇衍生物及其所有三个非对映异构体。该路线仅由市售Garner醛中的9个步骤组成。呋喃框架形成经由一个η 3 π-烯丙基中间体。

  DOI：

  10.1039/c0ob00643b

文献信息

• Stereoselective synthesis of Jaspine B and its C2 epimer from Garner aldehyde
  作者：Amit Kumar Jana、Gautam Panda

  DOI：10.1039/c3ra41778f

  日期：——

  Two different stereoselective routes for the synthesis of Jaspine B and its C2 epimer are presented here, starting from easily available Garner aldehyde. The key synthetic steps involved iodocyclization, organocuprate addition, HWE olefination, regioselective α-tosylation and cross metathesis reaction. This is the first report to synthesize Jaspine B involving iodocyclization.

  两种不同的立体选择性合成路线 茉莉花B从易于获得的Garner醛开始，这里介绍了它的C2差向异构体及其C2差向异构体。关键的合成步骤包括碘化，有机铜的加成，HWE烯化，区域选择性α-甲苯磺酸化和交叉复分解反应。这是第一份综合报告茉莉花B 涉及碘环化。
• Synthesis of pachastrissamine (jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis
  作者：Yuji Yoshimitsu、Jun Miyagaki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1016/j.tet.2013.03.091

  日期：2013.5

  An improved divergent synthesis of the four diastereomers of pachastrissamine from Garner's aldehyde has been reported. The common intermediate was synthesized by an indium-mediated acetoxyallylation reaction. The long alkyl side chain was introduced in the late stage of the synthesis using an olefin cross metathesis reaction. Biological evaluation of the chain modified analogs of the (2S,3S,4R)-isomer

  据报道，从加纳的醛中合成了四种帕斯帕司胺的非对映异构体的改进的发散性合成。常见的中间体是通过铟介导的乙酰氧基烯化反应合成的。在合成的后期，使用烯烃交叉复分解反应引入长烷基侧链。（2 S，3 S，4 R）-异构体的链修饰类似物的生物学评估表明，生物活性高度依赖于链长。
• Substrate and stereocontrolled iodocycloetherification of highly functionalized enantiomerically pure allylic alcohols: application to synthesis of cytotoxic 2-epi jaspine B and its biological evaluation
  作者：Somireddy Kundooru、Pintu Das、Sanjeev Meena、Vikash Kumar、Mohammad Imran Siddiqi、Dipak Datta、Arun K. Shaw

  DOI：10.1039/c5ob01123j

  日期：——

  Stereoselectivities of electrophilic additions of molecular iodine to enantiomerically pure highly functionalized allylic alcohols with internal nucleophiles have been investigated. The intramolecular nucleophilic attack on the I2–π complex by an oxygen nucleophile to obtain tri- and tetrasubstituted THFs is highly regio-, stereoselective and substrate controlled. The application of this study has

  已经研究了分子碘与对映体纯的高度官能化的烯丙基醇与内部亲核试剂的亲电子加成的立体选择性。氧亲核试剂对I 2- π配合物的分子内亲核攻击具有高度的区域选择性，立体选择性和受底物控制，从而获得三取代和四取代的THF。通过使用一种THF 4a作为关键中间体来完成海洋抗癌天然产物2- Epi jaspine B的全合成，表明了这项研究的应用。
• Novel sphingosine-containing analogues selectively inhibit sphingosine kinase (SK) isozymes, induce SK1 proteasomal degradation and reduce DNA synthesis in human pulmonary arterial smooth muscle cells
  作者：Hoe-Sup Byun、Susan Pyne、Neil MacRitchie、Nigel J. Pyne、Robert Bittman

  DOI：10.1039/c3md00201b

  日期：——

  Sphingosine 1-phosphate (S1P) is involved in hyper-proliferative diseases such as cancer and pulmonary arterial hypertension. We have synthesized inhibitors that are selective for the two isoforms of sphingosine kinase (SK1 and SK2) that catalyze the synthesis of S1P. A thiourea adduct of sphinganine (F02) is selective for SK2 whereas the 1-deoxysphinganines 55-21 and 77-7 are selective for SK1. (2S,3R)-1-Deoxysphinganine (55-21) induced the proteasomal degradation of SK1 in human pulmonary arterial smooth muscle cells and inhibited DNA synthesis, while the more potent SK1 inhibitors PF-543 and VPC96091 failed to inhibit DNA synthesis. These findings indicate that moderate potency inhibitors such as 55-21 are likely to have utility in unraveling the functions of SK1 in inflammatory and hyperproliferative disorders.

  Sphingosine 1-phosphate（S1P）参与了癌症和肺动脉高压等过度增生性疾病。我们合成了针对合成S1P的两个同工酶（SK1和SK2）的选择性抑制剂。Sphinganine（F02）的硫脲加合物对SK2具有选择性，而1-脱氧鞘氨醇55-21和77-7对SK1具有选择性。（2S，3R）-1-脱氧鞘氨醇（55-21）诱导了人肺动脉平滑肌细胞中SK1的蛋白酶体降解并抑制了DNA合成，而效力更强的SK1抑制剂PF-543和VPC96091未能抑制DNA合成。这些发现表明，如55-21这样的中等效力抑制剂可能在剖析SK1在炎症和过度增生性疾病中的功能方面具有应用价值。
• Enantioselective Synthesis of Jaspine B (Pachastrissamine) and Its C-2 and/or C-3 Epimers
  作者：Josep Llaveria、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1002/ejoc.201001477

  日期：2011.3

  Jaspine B and its C-2 and/or C3 epimers have been enantio-selectively prepared from butadiene monoepoxide through a synthetic procedure consisting of allylic amination by palladium-catalyzed dynamic kinetic asymmetric transformation, cross metathesis, and stereoselective dihydroxylation as key steps.

  Jaspine B 及其 C-2 和/或 C3 差向异构体已经从丁二烯单环氧化物通过合成程序对映选择性制备，该合成程序包括通过钯催化的动态动力学不对称转化、交叉复分解和立体选择性二羟基化的烯丙基胺化作为关键步骤。