D-xylo-phytosphingosine | 186907-22-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: D-xylo-phytosphingosine
• 英文别名: (2S,3R,4R)-2-aminooctadecane-1,3,4-triol
• CAS: 186907-22-2
• 化学式: C₁₈H₃₉NO₃
• 分子量: 317.513
• InChiKey: AERBNCYCJBRYDG-RCCFBDPRSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  483.7±40.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：

  D-xylo-phytosphingosine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 3.0h， 生成 [(2S,3R,4R)-2-(1,3-dioxobenzo[f]isoindol-2-yl)-3,4-bis(naphthalene-2-carbonyloxy)octadecyl] naphthalene-2-carboxylate
  参考文献：
  名称：

  植物鞘氨醇—一种用于构型分配的简便合成和光谱方案

  摘要：

  通过使用Wittig和Julia烯化反应，然后进行Sharpless二羟基化反应，已轻松合成了植物鞘氨醇的8种构型异构体中的4种。这四种立体异构体的集合用作模型化合物，用于开发用于分配所有植物鞘氨醇异构体的相对和绝对构型的通用化学/ CD / NMR方案。该程序基于两步衍生化为2- N-萘酰亚胺-1,3,4 - O-叔萘甲酸酯衍生物，这在选定的溶剂中产生了独特的激子耦合的圆二色性光谱和1 H-NMR光谱。光谱可用作参考数据，用于分配低鞘氨醇水平的植物鞘氨醇异构体和同类物的相对和绝对构型。

  DOI：

  10.1016/s0040-4020(99)00839-x
• 作为产物：
  描述：

  DL-2-Acetamido-1-acetoxy-trans-3-octadecen 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 D-xylo-phytosphingosine
  参考文献：
  名称：

  Syntheses of all of the racemic diastereoisomers of phytosphingosine

  摘要：

  DOI：

  10.1021/jo00827a013

文献信息

• Total Syntheses of D-xylo- and D-arabino-Phytosphingosine Based on the Syntheses of Chiral 1,3-Oxazines
  作者：Yu Mu、Tian Jin、Gun-Woo Kim、Jin-Seok Kim、Sung-Soo Kim、Yong-Shou Tian、Chang-Young Oh、Won-Hun Ham

  DOI：10.1002/ejoc.201200064

  日期：2012.5

  An efficient, stereocontrolled, and short synthetic method for the preparation D-xylo- and D-arabino-phytosphingsine was achieved utilizing chiral oxazines. The key features of this strategy are the stereoselective intramolecular oxazine formation catalyzed by palladium(0) and an intermolecular olefin cross-metathesis reaction.

  利用手性恶嗪实现了一种高效、立体控制且短的合成方法，用于制备 D-木-和 D-阿拉伯-植物鞘氨醇。该策略的关键特征是由钯 (0) 和分子间烯烃交叉复分解反应催化的立体选择性分子内恶嗪形成。
• Regioselective Inversion of the Hydroxyl Group in <scp>d</scp>-<i>ribo</i>-Phytosphingosine via a Cyclic Sulfate and Bis-Sulfonate Intermediate
  作者：Yun Mi Lee、Dong Jae Baek、Seokwoo Lee、Deukjoon Kim、Sanghee Kim

  DOI：10.1021/jo101757k

  日期：2011.1.21

  The selective synthesis of d-xylo- and d-lyxo-phytosphingosines from commercially available d-ribo-phytosphingosine is described. Thermolysis of the N-carbonyl protected cyclic sulfate led to an inversion of configuration of the proximal hydroxyl group to give the xylo-isomer, whereas the corresponding bis-sulfonate resulted in an inversion of configuration of the distal hydroxyl group to give the lyxo-isomer

  的选择性合成d - xylo-和d - L-来苏-phytosphingosines由市售d -核糖-phytosphingosine进行说明。热解的的Ñ羰基保护导致近端羟基的构的反转环状硫酸酯，得到木糖异构体，而相应的二磺酸酯导致在远端羟基的构型的转换，得到L-来苏-异构体。该研究允许在涉及羰基氧亲核试剂的分子内取代反应中比较环状硫酸盐和双磺酸盐。
• Synthesis and preliminary antifungal evaluation of a library of phytosphingolipid analogues
  作者：David Mormeneo、Josefina Casas、Amadeu Llebaria、Antonio Delgado

  DOI：10.1039/b709421c

  日期：——

  A library of 64 phytosphingolipid analogues resulting from the systematic variation of the C1, C3, C4, and the N-acyl moiety of phytosphingosine (PHS) has been prepared from common scaffolds derived from the chiral pool and Sharpless asymmetric dihydroxylation reactions. Library members have been evaluated as growth inhibitors of the yeast Saccaromyces cerevisiae. In addition, 1-amino-N-pivaloyl PHS analogues were also tested as IPC synthase inhibitors, in comparison with the natural product khafrefungin.

  已制备出一个由64种植物鞘氨醇类类似物组成的库，这些类似物是通过系统改变植物鞘氨醇（PHS）的C1、C3、C4和N-酰基基团而获得的，采用了源自手性池和Sharpless不对称二醇化反应的公共骨架。该库的成员作为酵母酿酒酵母（Saccaromyces cerevisiae）的生长抑制剂进行了评估。此外，还测试了1-氨基-N-哌喹酰PHS类似物，作为IPC合成酶抑制剂，并与天然产物khafrefungin进行比较。
• Synthetic C-glycolipid and its use for treating cancer, infectious diseases and autoimmune diseases
  申请人：——

  公开号：US20040127429A1

  公开（公告）日：2004-07-01

  The invention is directed to compounds of formula (I) 1 wherein X is O or NH; R′ is a hydrocarbon chain; R 3 and R 4 are hydrogen, OH or a monosaccharide; R 5 is hydrogen or a monosaccharide; Q′ is optionally present and may be a C 1-10 hydrocarbon; X′ is optionally present and may be O, S or NR 8 ; and Q 3 may be a hydrocarbon or hydrogen. The invention is also directed to the use of the compounds for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the compounds of formula (I).

  本发明涉及式(I)的化合物，其中X为O或NH; R′为一个碳氢链; R3和R4为氢、OH或单糖; R5为氢或单糖; Q′可选且可以是C1-10碳氢化合物; X′可选且可以是O、S或NR8; Q3可以是碳氢化合物或氢。本发明还涉及使用这些化合物治疗癌症、传染病和自身免疫性疾病。本发明还涉及制备式(I)化合物的方法。
• Synthetic C-glycolipid and its use for treating cancer, infectious diseases, and autoimmune diseases
  申请人：Tsuji Moriya

  公开号：US20060019246A1

  公开（公告）日：2006-01-26

  The invention is directed to compounds of formula (I) wherein X is O or NH; R′ is a hydrocarbon chain; R 3 and R 4 are hydrogen, OH or a monosaccharide; R 5 is hydrogen or a monosaccharide; Q′ is optionally present and may be a C 1-10 hydrocarbon; X′ is optionally present and may be O, S or NR 8 ; and Q 3 may be a hydrocarbon or hydrogen. The invention is also directed to the use of the compounds for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the compounds of formula (I).

  本发明涉及式（I）的化合物，其中X为O或NH；R′为一个碳氢链；R3和R4为氢、OH或单糖；R5为氢或单糖；Q′可选且可以是C1-10碳氢化合物；X′可选且可以是O、S或NR8；Q3可以是碳氢化合物或氢。本发明还涉及使用该化合物治疗癌症、传染病和自身免疫疾病。本发明还涉及式（I）化合物的合成。