18459-13-7

Upstream product

• 658-78-6 1-nitro-4-trifluoroacetoxy-benzene 
• 4201-60-9 3-O-benzoyl-D-erythro-sphingosine 
• 115464-01-2 (4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester 
• 131105-36-7 (2S,3R,4E)-N-trifluoroacetyl-1-O-trityl-4-sphingenine 
• 130967-71-4 N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide 
• 299172-58-0 3-O-benzoyl-N-tert-butoxycarbonyl-1-O-tritylsphingosine 
• 299172-62-6 (+)-tert-butyl {(1S,2R,3E)-2-Hydroxy-1-[(trityloxy)methyl]heptadec-3-en-1-yl}carbamate 
• 263558-18-5 tert-butyl 4-[(1R,2E)-1-benzoyloxyhexadec-2-enyl]-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 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 131105-37-8 (2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-1-O-trityl-4-sphingenine 

Downstream Products

• 299172-48-8 [glucose-(13)C6]-1-O-(β-D-glucopyranosyl)-D-erythro-sphingosine 
• 52050-17-6 Glucosylsphingosine 
• 299172-60-4 [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine 
• 131105-38-9 (2S,3R,4E)-3-O-benzoyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-4-sphingenine 

Relevant academic research and scientific papers

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.

Synthesis of Sphingosine Relatives, IX. Synthesis of (2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine. The Structure Proposed for the Esterified Cerebroside in the Epidermis of Guinea Pigs

(2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine (1) was synthesized from D-glucose (A), (2S,3R,4E)-4-sphingenine (sphingosine, B), 24-hydroxytetracosanoic acid (C) and linoleic acid (D).The 1H-NMR spectrum of the synthetic 1 was different from that of the esterified cerebroside which was isolated as a tissue-characteristic compound in the epidermis of foodpad and dorsal skin of guinea pigs.