26633-48-7

Upstream product

• 108-05-4 vinyl acetate 
• 142-94-9 2-bromostearic acid 
• 113773-89-0 cerebroside 
• 57-11-4 stearic acid 
• 112-76-5 Stearoyl chloride 
• 160186-22-1 (R)-3-octadecanoyl-4-benzyloxazolidin-2-one 

Downstream Products

• 100896-30-8 (2R)-2-hydroxyoctadecanoic acid methyl ester 
• 160147-98-8 (2S,2'R,3R,4E,8E)-N-2'-acetoxyoctadecanoyl-1-O-(β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine 
• 113773-89-0 cerebroside 
• 160147-91-1 p-nitrophenyl (R)-2-acetoxyoctadecanoate 

Relevant academic research and scientific papers

Stereoselective synthesis of unnatural (2S, 3S)-6-hydroxy-4-sphingenine-containing sphingolipids

6-Hydroxy-(4E)-sphingenine-containing sphingolipids are found in mammalian and bacterial membranes and have multiple intra- and intercellular functions. Most sphingolipids contain a (2S,3R)-2-amino-1,3-diol core structure, but only limited examples of unnatural (2S,3S)-2-amino-1,3-diol derivates have so far been reported. Using an underexplored hydrozirconation-transmetalation reaction and an unusual three-step-one-pot deprotection sequence, we were able to synthesize several unnatural (2S,3S)-6-hydroxy-(4E)-sphingenine-containing sphingolipids in only three (protected) or four (deprotected) consecutive steps, respectively, including a fluoresence-labeled derivative suitable for future biological studies.

First total synthesis of ganglioside DSG-A possessing neuritogenic activity

The first total synthesis of ganglioside DSG-A (1) is achieved via chemoselective glycosylation and a [1 + 1 + 2] synthetic strategy. We have also developed an efficient method that can be handled on large scale (50 g) for the synthesis of the phytosphingosine. This journal is

Cerebrosides from Fomitopsis pinicola (Sw. Ex Fr.) Karst.

A cerebroside fraction was obtained from the bruit bodies of fomitopsis pinicola using column chromatography and then separated into six compounds by reversed-phase HPLC.The sugar component of all cerebrosides was D-glucose.The major fatty acids were 2-hydroxyfatty acids (C14-C18), the long chain base was identified as 9-methyl-C18-4,8-sphingadienine which is widely distributed in fungi and reported to be essential for the fruit-inducing activity of fungi.Based on degradation studies, fast atom bombardment mass spectrometry, and different 1H and 13C NMR investigations, the structure of the main cerebroside (1) was determined to be (4E,8E,2S,3R,2'R)-N-2'-hydroxypalmityl-1-O-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine. - Keywords: Cerebroside; Glycolipid; Fomitopsis pinicola; 1H and 13C NMR

Synthesis of (2S,2'R,3R,4E,8E)-N-2'-Hydroxyoctadecanoyl-1-O-(β-D-glucopyranosyl)-9-methyl-4,8-sphingadienine (Pen III), a Cerebroside Isolated from Penicillium funiculosum as the Fruiting Inducer against Schizophyllum commune

(2S,2'R,3R,4E,8E)-N-2'-Hydroxyoctadecanoyl-1-O-(β-D-glucopyranosyl)-9-methyl-4,8-sphingadienine (Pen III), a cerebroside isolated from Penicillium funiculosum A-1 as the fruiting inducer against Basidiomycete Schizophyllum commune, was synthesized by starting from D-glucose, L-serine, homoprenyl acetate and stearic acid.