82970-80-7

Basic information

• Product Name: LYSO-SPHINGOMYELIN
• Synonyms: D-erythro/L-threo Lysosphingomyelin (d18:1)
• CAS NO: 82970-80-7
• Molecular Formula: C23H49N2O5P
• Molecular Weight: 464.623
• Mol File: 82970-80-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: LYSO-SPHINGOMYELIN(CAS DataBase Reference)
• NIST Chemistry Reference: LYSO-SPHINGOMYELIN(82970-80-7)
• EPA Substance Registry System: LYSO-SPHINGOMYELIN(82970-80-7)

Safety Data

• Hazardous Substances Data: 82970-80-7(Hazardous Substances Data)

Upstream product

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

Relevant articles and documents

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

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.

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