152142-06-8

Upstream product

• 335596-00-4 (2S,3R,4E)-3-benzoyloxy-2-methylsulfonyloxy-1-thexyldimethylsilyloxy-octadec-4-ene 
• 335595-99-8 (2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-ol 
• 149217-96-9 (2R,3R,4E)-2-azido-octadec-4-ene-1,3-diol 
• 6036-85-7 (2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol 
• 928302-06-1 (2R,3R,4E)-2-azido-1-(tert-butyldiphenylsilanyloxy)-octadec-4-en-3-ol 
• 928302-07-2 (1'R,1R,2E)-benzoic acid 1-[1'-azido-2'-(tert-butyldiphenylsilyloxy)-ethyl]-hexadec-2-enyl ester 

Downstream Products

• 928302-08-3 (1'R,1R,2E)-benzoic acid 1-[1'-azido-2'-(β-hepta-O-acetyllactosyl)-ethyl]-hexadec-2-enyl ester 

Relevant academic research and scientific papers

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.

A short and practical route to 3-O-benzoyl azidosphingosine

A short and practical route to 3-O-benzoyl azidosphingosine from D-xylose is described. The synthesis avoids the use of expensive and hazardous chemicals (i.e. mercury salts), and it is reproducible up to at least a 20 g scale. Furthermore, the synthesis proceeds to 3-O-benzoyl azidosphingosine with a minimum of protection group manipulation, by exploiting a regioselective protection of the primary HO-1 with thexyldimethylsilyl chloride.