137905-29-4

Basic information

• Product Name: 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE
• Synonyms: 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE;(2S,3R,4E)-2-AMINO-3-(TERTBUTYLDIMETHYLSILYLOXY)-4-OCTADECENE-1-OL
• CAS NO: 137905-29-4
• Molecular Formula: C24H51NO2Si
• Molecular Weight: 413.75
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 137905-29-4.mol

Chemical Properties

• Boiling Point: 482.728°C at 760 mmHg
• Flash Point: 245.745°C
• Appearance: /
• Density: 0.895g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.469
• Solubility: Acetone, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE(137905-29-4)
• EPA Substance Registry System: 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE(137905-29-4)

Safety Data

• Hazardous Substances Data: 137905-29-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE is used as a bioactive compound for its potential therapeutic applications. Its ability to selectively inhibit protein kinase C activity and phorbol dibutyrate binding makes it a promising candidate for the development of drugs targeting various diseases, particularly those involving abnormal cell signaling pathways.
Used in Research and Development:
In the field of research and development, 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE is used as a valuable tool for studying the roles of protein kinase C and other related enzymes in cellular processes. Its selective inhibition properties allow researchers to investigate the specific effects of these enzymes on cell function and contribute to a better understanding of their roles in health and disease.
Used in Drug Delivery Systems:
Similar to Gallotannin, 3-O-(TERT-BUTYLDIMETHYLSILYLOXY)-ERYTHRO-SPHINGOSINE can be employed in the development of novel drug delivery systems to enhance its applications and efficacy. By incorporating this compound into various carriers, such as organic and metallic nanoparticles, its delivery, bioavailability, and therapeutic outcomes can be improved, potentially leading to more effective treatments for various conditions.

InChI:InChI=1/C24H51NO2Si/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(22(25)21-26)27-28(5,6)24(2,3)4/h19-20,22-23,26H,7-18,21,25H2,1-6H3/b20-19+/t22-,23+/m0/s1

Upstream product

• 114299-64-8 (2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol 

Downstream Products

• 149035-77-8 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(9-fluorenylmethyloxycarbonylamino)-4-octadecene-1-ol 
• 536-14-1 N-palmitoyl-D-erythro-sphingomyelin 
• 144236-99-7 N-palmitoyl-D-erythro-sphingomyelin-1'-13C 
• 58909-84-5 sphingomyelin 
• 26993-30-6 Sphingosine-1-phosphate 

Relevant articles and documents

An efficient synthesis of sphingosine-1-phosphate

The total synthesis of D-erythro-sphingosine-1-phosphate (2) via the phosphoramidite approach, starting from 3-O-TBDMS-protected D-erythro-azidosphingosine 3 is described.

Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol

3-O-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-O-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.

An efficient route to N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives

We describe here a practical and efficient route to a homogeneous N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives. (2S, 3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octadecene-l-ol1 was converted to the sphingosine equivalent 2 by treatment with triphenylphosphine and water. Amine 2 was then coupled with palmitic acid, affording the ceramide derivative 3a. In the following two reactions the phosphorylcholine functional group was generated by using 2-chloro-2-oxo-1,3,2-dioxaphospholane and trimethylamine, respectively. The final deprotection of the secondary hydroxyl group in 5a produced the desired N palmitoyl D crythro sphingomyelin 6a. The overall yield of this five-step synthesis is 43%. The melting point, 213-215°C, the specific rotation, [α]20D - +6.8 (c= 1-3, CH2Cl2MeOH 1:1) and 1H-and 13C-NMR data indicate that the synthetic sphingomyelin is enantiomerically pure. The 13C-labeled derivatives 6b, 6c and 6d were synthesized by employing the same scheme.

A useful synthesis of D-erythro-sphingomyelins

A practical and efficient synthesis of N-palmitoyl-D-erythro-sphongomyelin is reported here, providing a general method for the preparation of various sphingomyelins bearing different N-acyl chains.