2482-37-3

Basic information

• Product Name: N,1-O,3-O-Triacetylsphingosine
• Synonyms: Acetic acid (2S,3R,4E)-2-(acetylamino)-3-acetoxy-4-octadecenyl ester;Diacetic acid (2S,3R,4E)-2-(acetylamino)-4-octadecene-1,3-diyl ester;N,1-O,3-O-Triacetylsphingosine;N,O,O-Triacetyl-C18-sphingosine;N-[(1S,2R,3E)-2-(Acetyloxy)-1-[(acetyloxy)methyl]-3-heptadecenyl]acetamide;N-[(1S,2R,3E)-2-Acetoxy-1-acetoxymethyl-3-heptadecenyl]acetamide
• CAS NO: 2482-37-3
• Molecular Formula: C₂₄H₄₃NO₅
• Molecular Weight: 425.6
• Mol File: 2482-37-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,1-O,3-O-Triacetylsphingosine(CAS DataBase Reference)
• NIST Chemistry Reference: N,1-O,3-O-Triacetylsphingosine(2482-37-3)
• EPA Substance Registry System: N,1-O,3-O-Triacetylsphingosine(2482-37-3)

Safety Data

• Hazardous Substances Data: 2482-37-3(Hazardous Substances Data)

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 108-24-7 acetic anhydride 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 195194-58-2 (2S,3R)-2-N-acetylamino-1,3-dihydroxyoctadec-4-ene 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 117112-63-7 (2S,3R,4E)-2-amino-1,3-benzylidene-4-octadecene-1,3-diol 
• 128387-01-9 (2S,3R,4Z)-1,3-diacetoxy-2-acetamido-octadec-4-ene 
• 472954-88-4 (2S,4E)-2-[N-(trityl)amino]-1-O-tert-butyldimethylsilyl-3-oxo-4-octadecene 
• 124-25-4 myristylaldehyde 
• 231291-79-5 (E)-(2S,3R)-2-(4-Methoxy-benzylamino)-octadec-4-ene-1,3-diol 
• 231291-87-5 (E)-1-[(S)-3-(4-Methoxy-benzyl)-2,2-dimethyl-oxazolidin-4-yl]-hexadec-2-en-1-one 
• 231291-93-3 ((E)-(S)-1-Hydroxymethyl-2-oxo-heptadec-3-enyl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester 
• 765-13-9 pentadec-1-yne 
• 78715-85-2 erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline 

Downstream Products

• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 13031-64-6 (2S,3R)-2-acetylaminooctadecan-1,3-diol 
• 3102-57-6 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3c-enyl)-acetamide 
• 81819-46-7 N-[(2R,4S,5R)-4-((E)-Pentadec-1-enyl)-2-phenyl-[1,3]dioxan-5-yl]-acetamide 

Relevant articles and documents

A diversity oriented synthesis of D-erythro-sphingosine and siblings

An efficient building block-based synthetic protocol has been developed for the synthesis of 3-ketosphingoids with various chain lengths using cross metathesis of a Garner's aldehyde-derived α,β-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided D-erythro-sphingosine and truncated anaogues in good overall yields.

Stereoselective synthesis of N,O,O,O-tetraacetyl-D-ribo-phytosphingosine, N,O,O-triacetyl-D-erythro-sphingosine and N,O,O-triacetyl sphingonine from a common chiral intermediate derived from D-mannitol

An efficient protocol for the stereoselective synthesis of tetraacetyl-D-ribo-hytosphingosine, triacetyl-D-erythro-sphingosine and triacetyl sphinganine has been devised from a common chiral intermediate derived from commercially available D-mannitol. The key steps involved are Sharpless epoxidation, Miyashita C(2) selective endo mode azide opening of 2,3-epoxy alcohol, and selective E-Wittig olefination. ARKAT-USA, Inc.

A rapid and efficient synthesis of D-erythro-sphingosine from D-ribo-phytosphingosine

In this paper we describe the concise synthesis of D-erythro-sphingosine starting from the readily available chiral building block D-ribo- phytosphingosine. The title compound is the ubiquitous sphingolipid from which most mammalian ceramides are derived. Our work is based on the existing literature in which the same sphingoid base is used as a starting point and culminates in what we believe is the most efficient synthesis of D-erythro-sphingosine reported to date.

A practical and cost-effective synthesis of d-erythro-sphingosine from d-ribo-phytosphingosine via a cyclic sulfate intermediate

The practical and efficient synthesis of d-erythro-sphingosine from commercially available d-ribo-phytosphingosine is described-. An important feature of this synthesis is the selective transformation of the 3,4-vicinal diol of phytosphingosine into the characteristic E-allylic alcohol of sphingosine via a cyclic sulfate intermediate that contains a non-nucleophilic trifluoroacetamide protecting group. Georg Thieme Verlag Stuttgart - New York.

Asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin via Miyashita C2 selective endo-mode azide opening of 2,3-epoxy alcohol

An efficient protocol for the asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin has been developed starting from commercially available propargyl alcohol. The key steps involved Sharpless asymmetric epoxidation and Miyashita C2 selective endo-mode azide opening of the 2,3-epoxy alcohol.

Asymmetric synthesis of vicinal amino alcohols: Xestoaminol C, sphinganine and sphingosine

The highly diastereoselective anti-aminohydroxylation of α,β-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps). The Royal Society of Chemistry 2008.

Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate

The synthesis of naturally occurring D-erythro-sphingosine and synthetically useful D-erythro-2-azidosphingosine from commercially available D-ribo-phytosphingosine is described. An important feature of this synthesis is the selective transformation of the 3,4-vicinal diol of phytosphingosine into the characteristic E-allylic alcohol of sphingosine via a cyclic sulfate intermediate.

Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine

Reaction of chiral guanidinium ylides with α,β-unsaturated aldehydes gives 3-(α,β-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(1-Methylvinyl)- and 3-[(E)-pentadec-1-enyl]aziridine-2- carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.

Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine

The synthesis of naturally occurring D-erythro-(2R,3S,4E)-sphingosine from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The key step in the reaction sequence comprises TMSI/DBN promoted regio- and stereoselective oxirane opening of intermediate 2-phenyl-4-(S)-[(1S,2S)-1,2- epoxyhexadecyl]-1,3-oxazoline followed by the in situ trans-elimination of 2-phenyl-4-(S)-[(1S,2R)-1,2-dideoxy-2-iodo-1-trimethylsilyloxyhexadecyl]-1, 3-oxazoline.

A process for the synthesis of sphingosine

This invention relates to a method for the production of a sphingoid base according to formula comprising the steps of(1) dissolving a starting compound according to formula III or a salt thereof in a substantially inert solvent,(2) protecting the NH2 group with a NH2 protecting group,(3) activating C4 HR3' for an elimination reaction with C5HR4,(4) causing an elimination reaction to take place to form a double bond between the C4 and C5 carbon atom,(5) removing the NH2 protecting group.