鞘氨醇和植物鞘氨醇化学合成的最新进展,Synthesis

鞘脂及其衍生物，例如鞘脂和鞘磷脂，在真核细胞的生物膜中是普遍存在的，它们在细胞增殖，识别，粘附和信号转导中起关键作用。鞘氨醇主要是糖鞘脂和鞘磷脂的重要脂质部分，而植物鞘氨醇是糖鞘脂的主要长链部分。由于这两种生物活性脂质的重要性，人们已经做出了巨大的努力来合成鞘氨醇或植物鞘氨醇，并采用了手性池方法，手性助剂和用于构建其连续立体异构中心的不对称反应。这篇综述涵盖了2000-2015年间发表的综合文献。

1引言

2手性方法

2.1糖的手性

2.2丝氨酸及其衍生物的手性

2.3 d-核糖-鞘氨醇的手性

2.4 d-酒石酸及其二酯的手性

2.5其他手性前体的手性

3手性助剂

3.1手性硫助剂

3.2手性含氮助剂

4个不对称反应

4.1无尖锐的二羟基化反应

4.2 Sharpless环氧化与Shi的环氧化反应

4.3不对称Aldol反应

4.4锐利的动力学分辨率

4.5不对称氨基羟基化和胺化

5。结论

鞘脂及其衍生物，例如鞘脂和鞘磷脂，在真核细胞的生物膜中是普遍存在的，它们在细胞增殖，识别，粘附和信号转导中起关键作用。鞘氨醇主要是糖鞘脂和鞘磷脂的重要脂质部分，而植物鞘氨醇是糖鞘脂的主要长链部分。由于这两种生物活性脂质的重要性，人们已经做出了巨大的努力来合成鞘氨醇或植物鞘氨醇，并采用了手性池方法，手性助剂和用于构建其连续立体异构中心的不对称反应。这篇综述涵盖了2000-2015年间发表的综合文献。

1引言

2手性方法

2.1糖的手性

2.2丝氨酸及其衍生物的手性

2.3 d-核糖-鞘氨醇的手性

2.4 d-酒石酸及其二酯的手性

2.5其他手性前体的手性

3手性助剂

3.1手性硫助剂

3.2手性含氮助剂

4个不对称反应

4.1无尖锐的二羟基化反应

4.2 Sharpless环氧化与Shi的环氧化反应

4.3不对称Aldol反应

4.4锐利的动力学分辨率

4.5不对称氨基羟基化和胺化

5。结论

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Sphingolipids and their derivatives, such as glycosphingolipids and sphingomyelins, are ubiquitous in the biomembrane of eukaryotic cells, and they play pivotal roles in cell proliferation, recognition, adhesion, and signal transduction. Sphingosine is predominantly the important lipid moiety of the glycosphingolipids and sphingomyelins, while phytosphingosine is a major long-chain moiety for glycosphingolipids. Due to the significance of these two bioactive lipids, tremendous efforts have been made to synthesize sphingosine or phytosphingosine, with chiral pool approaches, chiral auxiliaries, and asymmetric reactions used to construct their contiguous stereogenic centers. This review covers the synthetic literature published from 2000–2015.

1 Introduction

2 Chiral Approach

2.1 Chirality from Sugars

2.2 Chirality from Serine and Its Derivatives

2.3 Chirality from d-ribo-Phytosphingosine

2.4 Chirality from d-Tartaric Acid and Its Diester

2.5 Chirality from Other Chiral Precursors

3 Chiral Auxiliaries

3.1 Chiral Sulfur Auxiliaries

3.2 Chiral N-Containing Auxiliaries

4 Asymmetric Reactions

4.1 Sharpless Dihydroxylation Reaction

4.2 Sharpless Epoxidation and Shi’s Epoxidation Reaction

4.3 Asymmetric Aldol Reaction

4.4 Sharpless Kinetic Resolution

4.5 Asymmetric Aminohydroxylation and Amination

5 Conclusions

Sphingolipids and their derivatives, such as glycosphingolipids and sphingomyelins, are ubiquitous in the biomembrane of eukaryotic cells, and they play pivotal roles in cell proliferation, recognition, adhesion, and signal transduction. Sphingosine is predominantly the important lipid moiety of the glycosphingolipids and sphingomyelins, while phytosphingosine is a major long-chain moiety for glycosphingolipids. Due to the significance of these two bioactive lipids, tremendous efforts have been made to synthesize sphingosine or phytosphingosine, with chiral pool approaches, chiral auxiliaries, and asymmetric reactions used to construct their contiguous stereogenic centers. This review covers the synthetic literature published from 2000–2015.

1 Introduction

2 Chiral Approach

2.1 Chirality from Sugars

2.2 Chirality from Serine and Its Derivatives

2.3 Chirality from d-ribo-Phytosphingosine

2.4 Chirality from d-Tartaric Acid and Its Diester

2.5 Chirality from Other Chiral Precursors

3 Chiral Auxiliaries

3.1 Chiral Sulfur Auxiliaries

3.2 Chiral N-Containing Auxiliaries

4 Asymmetric Reactions

4.1 Sharpless Dihydroxylation Reaction

4.2 Sharpless Epoxidation and Shi’s Epoxidation Reaction

4.3 Asymmetric Aldol Reaction

4.4 Sharpless Kinetic Resolution

4.5 Asymmetric Aminohydroxylation and Amination

5 Conclusions