299172-59-1

Usage

Chemical Properties

White Crystalline Solid

Upstream product

• 263558-18-5 tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-2,2-dimethyloxazolidine-3-carboxylate 
• 115464-01-2 (4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester 
• 13360-61-7 1-pentadecene 
• 114301-34-7 tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 115464-04-5 tert-butyl (4S)-4-[(1S,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 65-85-0 benzoic acid 
• 115464-03-4 tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 1204403-20-2 (2S,3R,E)-3-O-benzoyl-2-(tert-butoxycarbonyl)amido-1-(tert-butyldiphenylsilyloxy)-4-octadecene-1,3-diol 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 74365-77-8 glucosylceramide 
• 896444-03-4 C₅₈H₇₇NO₁₁ 
• 381716-44-5 Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-1-octadecanoylamino-ethyl}-hexadec-2-enyl ester 
• 381715-17-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol 
• 381715-20-4 [(1S,2R)-2-Hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl]-carbamic acid tert-butyl ester 
• 381715-12-4 (2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol 

Relevant academic research and scientific papers

Synthesis of a panel of carbon-13-labelled (glyco)sphingolipids

The synthesis of a focussed library of sphingolipids differing in the number and position of 13C labels is described. The synthesised sphingolipids differ in substitution at both the sphingosine amine (either palmitoylated or unmodified) and the sphingosine primary hydroxyl (unmodified or glycosylated). Moreover, 13C atoms are incorporated into either the sphingosine or the palmitate moiety, or both. This set of compounds is intended for use in relative quantitative lipidomics studies to gain insight into sphingolipid metabolism in healthy and diseased (lysosomal storage disorders) patients and animal models. The synthesis of a focussed library of sphingolipids differing in the number and position of 13C labels is described. 13C atoms are incorporated into either the sphingosine or the palmitate moiety, or both. This set of compounds is intended for use in relative quantitative lipidomics studies to gain insight into sphingolipid metabolism.

Practical syntheses of [13C]- and [14C]-labelled glucosphingolipids

Synthetic routes to [glucose-U-14C]-1-O-(β-D-glucopyranosyl)-N-stearoyl-D-erythro-sp hingosine 1b and to [glucose-13C6]-1-O-(β-D-glucopyranosyl)sphingosine ([glucose-13C6]glucopsychosine, 2b) are described. Whereas the protected ceramide precursor for lb was prepared using conventional methodology, two new strategies were developed in the course of the synthesis of 2b. Of these, one relies on keeping a protecting group in place at all times to avoid the handling difficulties associated with sphingosine 4, while the other generates a protected derivative (24) of sphingosine indirectly by means of a Mitsunobu inversion.