197144-08-4

Basic information

• Product Name: Benzoic acid (E)-(R)-1-{(S)-1-azido-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester
• Synonyms: Benzoic acid (E)-(R)-1-{(S)-1-azido-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester
• CAS NO: 197144-08-4
• Molecular Weight: 976.085
• Mol File: 197144-08-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid (E)-(R)-1-{(S)-1-azido-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (E)-(R)-1-{(S)-1-azido-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester(197144-08-4)
• EPA Substance Registry System: Benzoic acid (E)-(R)-1-{(S)-1-azido-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester(197144-08-4)

Safety Data

• Hazardous Substances Data: 197144-08-4(Hazardous Substances Data)

Upstream product

• 197144-05-1 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(3R,4S,5R,6S)-4,5-diacetoxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 

Downstream Products

• 197144-09-5 Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R)-3,4-diacetoxy-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 

Relevant articles and documents

Synthesis of XylβCer, Galβ1-4XylβCer, NeuAcα2-3Galβ1-4XylβCer and the Corresponding Lactone and Lactam Trisaccharides

2-(Trimethylsilyl)ethyl 2-O-benzoyl- and 2,3-di-O-acetyl-β-D-xylopyranosides (12 and 14) were synthesized in high yields and subjected to glycosylation with various glycosyl donors. Galactosylation of 12 gave the xylose analogue of TMSEt lactoside (3), which was transformed into the glycosyl acceptor 19. Sialylation then gave the xylose analogue of GM3 trisaccharide (5). The TMSEt glycosides 10, 25, and 32 were transformed into the corresponding trichloroacetimidates, which were used for glycosylation of an azidosphingosine derivative. The resulting sphingosyl glycosides were transformed into the title ceramides. Treatment of NeuAcα2-3Galβ1-4XylβCer (5) with acetic acid gave the corresponding 1″→2′-lactone 7. Glycosylation of 12 or 14 with a GM4-lactam donor (40) gave the xylose analogue of GM3-lactam (42). There was a 3-fold increase in the formation of GAG chains in the presence of 0.5 μM XylβCer (2) in the medium.