L-ribo-phytosphingosine | 183253-71-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: L-ribo-phytosphingosine
• 英文别名: (2R,3R,4S)-2-aminooctadecane-1,3,4-triol；phytosphingosine；1,3,4-Octadecanetriol, 2-amino-, (2R,3R,4S)-
• CAS: 183253-71-6
• 化学式: C₁₈H₃₉NO₃
• 分子量: 317.513
• InChiKey: AERBNCYCJBRYDG-FGTMMUONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-ribo-phytosphingosine 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Bioactive lipids from the sponge Spirastrella abata

  摘要：

  Three sphingosine 4-sulfates (1-3) and a lysophosphatidylglycerol (4) were isolated from the Korean sponge Spirastrella abata. The structures of these compounds were determined based on the combined results of spectroscopic analyses. Based on the results of combined synthesis and comparison of specific rotation and circular dichroism, the absolute configurations of 1-3 were found to be enantiomeric to the previously isolated metabolites. The configurations of 4 were also partially determined by similar chemical and spectroscopic methods. The compounds exhibited significant cytotoxicity and weak antimicrobial activity (1), as well as weak-to-moderate inhibitory activity against isocitrate lyase and Na+/K+-ATPase. A structure-activity relationship was found for the sphingosine 4-sulfates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.105
• 作为产物：
  描述：

  (2S,3S,4R)-2-Amino-1-tert-butoxy-octadecane-3,4-diol 在 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 、 氨 为溶剂， 以81%的产率得到L-ribo-phytosphingosine
  参考文献：
  名称：

  Schwab, Wilfried; Jaeger, Volker, Angewandte Chemie, 1981, vol. 93, # 6/7, p. 578 - 579

  摘要：

  DOI：

文献信息

• Divergent total synthesis of d-ribo-phytosphingosine and l-ribo-phytosphingosine from d-ribose
  作者：Jong Soo Chun、Seung Min Hong、Tae Hong Jeon、Sook Jin Park、Han Pyo Son、Jun Min Jung、Young Jae Choi、In Su Kim、Young Hoon Jung

  DOI：10.1016/j.tet.2016.11.018

  日期：2016.12

  Divergent total synthesis of d-ribo-phytosphingosine (1) and l-ribo-phytosphingosine (2) was achieved from readily available d-ribose via cross-metathesis reaction, Wittig reaction, and diastereoselective amination reaction of allylic ethers using chlorosulfonyl isocyanate (CSI) as the key steps. As results, reactions of anti-1,2-dibenzyl ethers 11 and 16 with chlorosulfonyl isocyanate afforded exclusively

  的发散总合成d -核糖-phytosphingosine（1）和升-核糖-phytosphingosine（2）从容易获得的取得d -核糖通过交叉复分解反应，Wittig反应，并用磺酰异氰酸酯的烯丙基醚的非对映选择性的氨基化反应（CSI ）作为关键步骤。结果，抗-1,2-二苄基醚11和16与氯磺酰基异氰酸酯反应，仅得到抗-1,2-氨基醇12和17。非对映选择性为32：1和31：1，产率分别为75％和76％。这些结果可以通过邻近基团效应来解释，从而导致立体化学的保留。
• Achieving Molecular Complexity by Organocatalytic One-Pot Strategies-A Fast Entry for Synthesis of Sphingoids, Amino Sugars, and Polyhydroxylated α-Amino Acids
  作者：Hao Jiang、Petteri Elsner、Kim L. Jensen、Aurelia Falcicchio、Vanesa Marcos、Karl Anker Jørgensen

  DOI：10.1002/anie.200901446

  日期：2009.9.1

  Simple complexity: By developing an organocatalyzed chiral leaving group strategy, molecular complexity was rapidly and efficiently achieved from simple starting materials. The 4,5‐disubstituted isoxazoline‐N‐oxide products, obtained in high yield and enantioselectivity from an organocatalyzed one‐pot, three‐step sequence, served as versatile building blocks for natural products (see scheme).

  简单的复杂性：通过开发有机催化的手性离去基团策略，可以从简单的起始原料快速有效地实现分子的复杂性。4,5-二取代的异恶唑啉-N-氧化物产品是从有机催化的一锅三步程序中以高收率和对映选择性获得的，可作为天然产物的通用组成部分（请参见方案）。
• Synthesis of racemic phytosphingosine and the lyxo isomer
  作者：Keiiti Sisido、Noriyuki Hirowatari、Tyuzo Isida

  DOI：10.1021/jo01263a068

  日期：1969.11
• MERRILL, ALFRED H. , JR.;JR.;WANG, ELAINE;MULLINS, RICHARD E.;CHARLES, W.+, ANAL. BIOCHEM., 171,(1988) N 2, 373-381
  作者：MERRILL, ALFRED H. , JR.、JR.、WANG, ELAINE、MULLINS, RICHARD E.、CHARLES, W.+

  DOI：——

  日期：——