82970-80-7

Upstream product

• 860021-45-0 (4S)-4-[(1R)-1-(tert-butyldiphenylsilyloxy)-hexadec-2-enyl]-2-chloro-2-oxo-[1,3,2]-oxazaphospholidine 
• 55357-38-5 choline tosylate 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 10257-28-0 D-Galactose 
• 3006-41-5 4,6-O-benzylidene-α,β-D-galactopyranose 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 103348-49-8 2-azido-sphingosine 
• 916159-70-1 (2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol 
• 168411-99-2 <(2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-yl><2-(trimethylammonio)ethyl> phosphate 

Relevant academic research and scientific papers

An Improved, Versatile, and Easily Scalable Synthesis of Sphingomyelins: Application to Stable Isotope Labeling

With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3- O -benzoylsphingos

Newly Synthesized Lipid–Porphyrin Conjugates: Evaluation of Their Self-Assembling Properties, Their Miscibility with Phospholipids and Their Photodynamic Activity In Vitro

Lipid–porphyrin conjugates are considered nowadays as promising building blocks for the conception of supramolecular structures with multifunctional properties, required for efficient cancer therapy by photodynamic therapy (PDT). The synthesis of two new lipid–porphyrin conjugates coupling pheophorbide-a (Pheo-a), a photosensitizer derived from chlorophyll-a, to either chemically modified lyso-phosphatidylcholine (PhLPC) or egg lyso-sphingomyelin (PhLSM) is reported. The impact of the lipid backbone of these conjugates on their self-assembling properties, as well as on their physicochemical properties, including interfacial behavior at the air/buffer interface, fluorescence and absorption properties, thermotropic behavior, and incorporation rate in the membrane of liposomes were studied. Finally, their photodynamic activity was evaluated on esophageal squamous cell carcinoma (ESCC) and normal esophageal squamous epithelium cell lines. The liposome-like vesicles resulting from self-assembly of the pure conjugates were unstable and turned into aggregates with undefined structure within few days. However, both lipid–porphyrin conjugates could be efficiently incorporated in lipid vesicles, with higher loading rates than unconjugated Pheo-a. Interestingly, phototoxicity tests of free and liposome-incorporated lipid–porphyrin conjugates demonstrated a better selectivity in vitro to esophageal squamous cell carcinoma relative to normal cells.

SPHINGOMYELIN, INTERMEDIATES THEREOF AND METHODS FOR PREPARATION OF SAME

The invention concerns novel oxazaphospholanes, cyclic and acyclic, and to their use in the synthesis of sphingomyelin and sphingomyelin analogous as well as to synthetic sphingomyelins obtained therefrom. One group of oxazaphospholane according to the invention has the general formula (1) disclosed herein. Specifically, the invention provides the 2S, 3R stereoisomers of the disclosed oxazaphospholanes and sphingomyelins and synthetic methods for their preparation.

Process for the preparation of cyclic 4-oxoamidines

The present invention relates to a process for the preparation of cyclic 4-oxoamidines. Such substances are precursors of active substances having biological action. The process according to the invention forms a further method of obtaining this class of compound. By reacting condensation products of aldehydes and aminonitriles or amino acid amides with oxidizing agents, the desired cyclic 4-oxoamidines are obtained according to the invention in good to very good yields.

Efficient Synthesis of Sphingosine-1-phosphate, Ceramide-1-phosphate, Lysosphingomyelin, and Sphingomyelin

Readily available D-erythro-azidosphingosine is transformed into 3-O-silyl-protected derivative 6.Reduction of the azido group afforded 3-O-silyl-protected sphingosine 7 which was either converted into N-Fmoc-protected derivative 8 or via N-acylation into ceramide derivatives 16 and 17, respectively.Treatment of 6, 8, and 16 with bis(2-cyanoethoxy)(diisopropylamino)phosphane as monofunctional phsophitylating agent, subsequent oxidation and then removal of the protective groups furnished azidosphingosine-1-phosphate (11), sphingosine-1-phosphate (2), and ceramide-1-phosphate (4), respectively.Treatment of 8 and 17 with bis(diisopropylamino)(2-cyanoethoxy)phosphane as bifunctional phosphitylating agent and then with choline afforded after oxidation and subsequent deprotection lysosphingomyelin (3) and sphingomyelin (1), respectively in high overall yields.All final products are sterochemically pure and possess D-erythro configuration in the sphingosine moiety. - Key Words: Phosphosphingolipids, synthesis of/ Azidosphingosine/ Azidosphingosine-1-phosphate/ Phosphitylation/ Sphingosine phosphates