114200-61-2

Basic information

• Product Name: (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol
• Synonyms: (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol
• CAS NO: 114200-61-2
• Molecular Weight: 890.209
• Mol File: 114200-61-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol(114200-61-2)
• EPA Substance Registry System: (2S,3R,4E,8E)-2-<(2R)-2-<(2R)-2-Acetoxy-2-phenylacetoxy>hexadecanoylamino>-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol(114200-61-2)

Safety Data

• Hazardous Substances Data: 114200-61-2(Hazardous Substances Data)

Upstream product

• 114200-59-8 (2S,3R,4E,8E)-2-Amino-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol 
• 114200-60-1 (R)-2-((R)-2-Acetoxy-2-phenyl-acetoxy)-hexadecanoic acid 
• 114200-57-6 (2S,3R,4E,8E)-2-Azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4,8-octadecadien 
• 114200-50-9 (E)-4-Tetradecenyl-triphenylphosphoniumbromid 
• 114200-55-4 (2S,3R,4E,8E)-2-Azido-3-benzoyloxy-1-triphenylmethyloxy-4,8-octadecadien 
• 114200-54-3 (2S,3R,4E,8E)-2-Azido-1-triphenylmethyloxy-4,8-octadecadien-3-ol 
• 114200-58-7 (2S,3R,4E,8E)-2-Azido-1-(β-D-glucopyranosyloxy)-4,8-octadecadien-3-ol 
• 114200-56-5 (2S,3R,4E,8E)-2-Azido-3-benzoyloxy-4,8-octadecadien-1-ol 
• 114200-52-1 (2S,3R,4E,8E)-2-Azido-1,3-O-benzyliden-4,8-octadecadien-1,3-diol 
• 114200-51-0 (2R,3R,4E,8E)-1,3-O-Benzyliden-4,8-octadecadien-1,2,3-triol 
• 114200-53-2 (2S,3R,4E,8E)-2-Azido-4,8-octadecadien-1,3-diol 
• 114200-49-6 (E)-1-bromo-4-tetradecene 
• 114200-48-5 (4E)-4-Tetradecensaeure-methylester 
• 4048-42-4 1-dodecen-3-ol 

Downstream Products

• 114297-20-0 (2′R)-N-{(1S,2R,3E,7E)-1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxyheptadeca-3,7-dien-1-yl}-2-hydroxyhexadecanamide 

Relevant articles and documents

Glycosyl Imidates, 35. - Synthesis of a Cerebroside Having a (4E,8E)-Sphingadienine Moiety from Tetragonia tetragonoides with Antiulcerogenic Activity

The natural cerebroside 1a possessing antiulcerogenig activity and its diastereomer 1b were readily synthesized by the azidosphingosine glycosylation method.The requied (4E,8E)-azidosphingadienine 12 was obtained from (4E)-tetradecenyl bromide (7) and 2,4-O-benzylidene-D-threose (9) by Wittig reaction, subsequent azide introduction and benzylidene group removal.For the glucosylation the corresponding 3-O-benzoyl derivative 15 was prepared; it provided with the trichloroacetimidate 16 as glucosyl donor the desired β-D-glucopyranosyl derivative 17 in high yield.Deprotection and azido group reduction afforded compound 19 with a free amino group.N-Acylation with both enantiomers of 2-hydroxypalmitic acid (using the derivatives 20 a,b) yielded after deacetylation compounds 1a and 1b, respectively.