(2S,3S,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate | 471877-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (2S,3S,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate
• 英文别名: N,O-diacetyljaspine B；[(2S,3S,4S)-4-acetamido-2-tetradecyloxolan-3-yl] acetate
• CAS: 471877-78-8
• 化学式: C₂₂H₄₁NO₄
• 分子量: 383.572
• InChiKey: LUFXSTBCUCLTGY-FKBYEOEOSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  515.3±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate 在 甲醇 、 水 、 三乙胺 作用下， 生成 N-acylated-JB
  参考文献：
  名称：

  Jaspines A and B: two new cytotoxic sphingosine derivatives from the marine sponge Jaspis sp.

  摘要：

  The ethanolic extract of the sponge Jaspis sp. collected in Vanuatu showed cytotoxicity against KB tumour cells (IC95 = 10 mug/ml). A bioassay-guided fractionation led to the isolation of two new cytotoxic sphingosine derivatives, jaspine A and jaspine B. Structures were elucidated by spectroscopic methods, and absolute configuration by chemical derivatisation. The cytotoxicity of jaspine B hydrochloride was evaluated against the A549 lung tumour cell line (IC50 = 3.4 x 10(-7) M). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02541-8
• 作为产物：
  描述：

  糖脂 在 吡啶 、 triflic azide 、 三氟化硼乙醚 、 potassium tert-butylate 、 potassium carbonate 、 copper(II) sulfate 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 57.0h， 生成 (2S,3S,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  An Efficient Synthesis of the Natural Tetrahydrofuran Pachastrissamine Starting from d-ribo-Phytosphingosine

  摘要：

  [GRAPHICS]The natural product pachastrissamine, an anhydrophytosphingosine derivative isolated from various sponges and endowed with cytotoxic activity against several human carcinoma cell lines, was synthesized in three steps and with 72% overall yield from D-ribo-phytosphingosine.

  DOI：

  10.1021/jo0520240

文献信息

• Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition
  作者：Elin Abraham、E. Anne Brock、José I. Candela-Lena、Stephen G. Davies、Matthew Georgiou、Rebecca L. Nicholson、James H. Perkins、Paul M. Roberts、Angela J. Russell、Elena M. Sánchez-Fernández、Philip M. Scott、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b801671b

  日期：——

  The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine (20% yield over 7 steps)

  （E）-γ-三异丙基甲硅烷氧基-α，β-不饱和酯的高度非对映选择性抗氨基羟基化反应，方法是共轭添加（S）-N-苄基-N-（α-甲基苄基）锂（+）-（樟脑磺酰基）恶唑烷的原位烯醇氧化已被用作N，O，O，O-四乙酰基d-lyxo-physphingosine的不对称合成的关键步骤（7步收率20％），脱水植物鞘氨醇茉莉B（9步中的收率为10％），2-表麻B（9步中的收率为14％）和Prosopis生物碱脱氧脯氨酸茶碱（7步中的收率为26％）。
• Enantioselective Synthesis of Pachastrissamine (Jaspin B) Using Dirhodium(II)-Catalyzed C-H Amination and Asymmetric Dihydroxylation as Key Steps
  作者：Takayuki Yakura、Seiichi Sato、Yuya Yoshimoto

  DOI：10.1248/cpb.55.1284

  日期：——

  Enantioselective total synthesis of anhydrophytosphingosine pachastrissamine (jaspin B) was achieved using Sharpless asymmetric dihydroxylation and dirhodium(II)-catalyzed C–H amination as key steps.

  通过使用Sharpless不对称二羟基化和二铑(II)催化的C-H胺化作为关键步骤，成功实现了无水植物鞘氨醇巴克斯特胺（jaspin B）的对映选择性全合成。
• Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
  作者：Elin Abraham、José I. Candela-Lena、Stephen G. Davies、Matthew Georgiou、Rebecca L. Nicholson、Paul M. Roberts、Angela J. Russell、Elena M. Sánchez-Fernández、Andrew D. Smith、James E. Thomson

  DOI：10.1016/j.tetasy.2007.10.026

  日期：2007.10

  The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer.

  （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。
• Synthesis of Pachastrissamine from Phytosphingosine:  A Comparison of Cyclic Sulfate vs an Epoxide Intermediate in Cyclization
  作者：Taeho Lee、Sukjin Lee、Young Shin Kwak、Deukjoon Kim、Sanghee Kim

  DOI：10.1021/ol062756u

  日期：2007.2.1

  [reaction: see text] The syntheses of the cytotoxic natural product pachastrissamine and its unnatural 4-epi-congener were accomplished starting from a natural phytosphingosine. The relatively unstrained cyclic sulfate intermediate smoothly underwent the 5-endo cyclization to yield the 2,3,4-trisubstituted tetrahydrofuran ring system of pachastrissamine. The corresponding epoxy alcohol afforded the

  [反应：见正文]细胞毒性天然产物Pachastrissamine及其非天然的4-epi-同源物的合成是从天然的植物鞘氨醇开始的。相对未应变的环状硫酸盐中间体顺利地进行了5内环化，生成了2个3，4，4-三取代的四氢呋喃环糊精。相应的环氧醇通过甲苯磺酸酯介导的双转化过程提供了4-表异构体。
• Stereoselective synthesis of pachastrissamine (jaspine B)
  作者：Celia Ribes、Eva Falomir、Miguel Carda、J.A. Marco

  DOI：10.1016/j.tet.2006.03.073

  日期：2006.6

  A stereoselective synthesis in enantiopure form of the natural anhydrophytosphingosine pachastrissamine (jaspine B), a metabolite isolated from sponges, is described. The chiral epoxide (R)-glycidol was the starting material. Key steps of this synthesis are a Sharpless asymmetric epoxidation, an intramolecular stereospecific epoxide opening mediated by a trichloroacetimidate group, and the formation

  描述了对映体纯形式的天然脱水植物鞘氨醇pachastrissamine（jaspine B），一种从海绵中分离出来的代谢物的立体选择性合成。手性环氧化物（R）-缩水甘油是起始原料。该合成的关键步骤是无尖锐的不对称环氧化，由三氯乙酰亚胺酸酯基团介导的分子内立体特异性环氧化物开环和通过分子内亲核取代形成四氢呋喃环。