108283-58-5

Basic information

• Product Name: (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol
• Synonyms: (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol
• CAS NO: 108283-58-5
• Molecular Weight: 671.923
• Mol File: 108283-58-5.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol(108283-58-5)
• EPA Substance Registry System: (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol(108283-58-5)

Safety Data

• Hazardous Substances Data: 108283-58-5(Hazardous Substances Data)

Upstream product

• 112-71-0 1-Bromotetradecane 
• 104826-31-5 <2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol 
• 104826-27-9 <2(R),3(R),4E>-1,3-O-isopropylidene-4-octadecene-1,2,3-triol 
• 76-83-5 trityl chloride 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 124313-98-0 (2R,3R,4E)-1,3-benzylidene-2-methanesulfonyl-4-octadecene-1,2,3-triol 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 103348-49-8 2-azido-sphingosine 
• 108283-57-4 (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 4201-63-2 (2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 172340-52-2 Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 108283-59-6 (2S,3R,4E)-2',3',4',6'-tetraacetyl-β-D-glucopyranosyl-(1'<->1)-2-azido-3-benzoyl-4-octadecene-1,3-diol 
• 74365-77-8 glucosylceramide 
• 52050-17-6 Glucosylsphingosine 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 

Relevant articles and documents

The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog

The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.

Synthesis of Sphingosines, 4. - Synthesis of erythro-Sphingosines via Their Azido Derivatives

The 2,4-O-protected D-threoses 3a and 3b were obtained from D-galactose and D-xylose, respectively, in two-step procedures.Wittig reaction in the presence of an excess of lithium bromide afforded the trans-enetriols 4aA, 4aB, and 4bA.Triflate activation of the unprotected 2-hydroxy group, azide group introduction, and cleavage of the O-protective groups yielded the azidosphingosines 6A,B which provide after azide group reduction the D-erythro-sphingosines 7A,B.For the glycosphingolipid synthesis through azidosphingosine glycosylation, compound 6A was transformed by 1-O tritylation, 3-O protection, and subsequent 1-O detritylation into the 3-O-protected azidosphingosines 11α-11γ.