928302-11-8

Basic information

• Product Name: 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2R,3S,4E)-
• CAS NO: 928302-11-8
• Molecular Formula: C34H53N3O2Si
• Molecular Weight: 563.899
• Mol File: 928302-11-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2R,3S,4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2R,3S,4E)-(928302-11-8)
• EPA Substance Registry System: 4-Octadecen-3-ol, 2-azido-1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2R,3S,4E)-(928302-11-8)

Safety Data

• Hazardous Substances Data: 928302-11-8(Hazardous Substances Data)

Upstream product

• 6036-75-5 (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 
• 130511-47-6 (2R,3S,4E)-2-azido-octadec-4-ene-1,3-diol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 137896-83-4 (1'R,1S,2E)-benzoic acid 1-(1'-azido-2'-hydroxyethyl)hexadec-2-enyl ester 
• 928302-13-0 (1'R,1S,2E)-benzoic acid 1-[1'-azido-2'-(β-hepta-O-acetyllactosyl)-ethyl]-hexadec-2-enyl ester 
• 928302-12-9 (1'R,1S,2E)-benzoic acid 1-[1'-azido-2'-(tert-butyldiphenylsilyloxy)-ethyl]-hexadec-2-enyl ester 

Relevant articles and documents

Synthesis of fluorescent lactosylceramide stereoisomers

The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or d-erythro-)-β-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-1-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY)-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake.