35301-24-7

Basic information

• Product Name: Cedefingol
• Synonyms: Cedefingol
• CAS NO: 35301-24-7
• Molecular Formula: C20H41NO3
• Molecular Weight: 343.548
• Mol File: 35301-24-7.mol

Chemical Properties

• Boiling Point: 531.843°C at 760 mmHg
• Flash Point: 275.449°C
• Appearance: /
• Density: 0.953g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: Cedefingol(CAS DataBase Reference)
• NIST Chemistry Reference: Cedefingol(35301-24-7)
• EPA Substance Registry System: Cedefingol(35301-24-7)

Safety Data

• Hazardous Substances Data: 35301-24-7(Hazardous Substances Data)

Usage

Uses

Antineoplastic (adjunct); antipsoriatic.

InChI:InChI=1/C20H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h19-20,22,24H,3-17H2,1-2H3,(H,21,23)/t19-,20-/m0/s1

Upstream product

• 35301-20-3 N,O,O-triacetyl-L-threo-C₁₈-dihydrosphingosine 
• 3102-56-5 dihydrosphingosine 
• 75-36-5 acetyl chloride 
• 111168-14-0 erythro-3-amino-2-iodo-octadecan-1-ol hydrochloride 
• 111168-23-1 trans-2-hydrxymethyl-3-pentadecylaziridine 
• 13552-13-1 threo-2-acetamido-1,3-diacetoxyoctadecane 
• 111168-24-2 ((2S,3S)-3-Pentadecyl-aziridin-2-yl)-methanol; hydrochloride 
• 764-22-7 (+/-)-threo-dihydro-sphingosine 
• 4444-84-2 (+/-)-threo-2,3-epoxy-octadecanoic acid 
• 14663-15-1 (+/-)-erythro-2-benzylamino-octadecane-1,3-diol 
• 51767-87-4 1-Acetylamino-2-heptadecanon 
• 108-24-7 acetic anhydride 
• 13031-65-7 3-Oxo-1-hydroxy-2-acetamidooctadecan 
• 107649-72-9 2-N-acetamide-hexadecanoyl-acetic acid methyl ester 

Downstream Products

• 3102-56-5 dihydrosphingosine 

Relevant articles and documents

Development of Asymmetric Transfer Hydrogenation with a Bifunctional Oxo-Tethered Ruthenium Catalyst in Flow for the Synthesis of a Ceramide (D-erythro-CER[NDS])

The development of an efficient synthetic route for an optically active ceramide compound (d-erythro-CER[NDS]) is described. The route proceeds through asymmetric transfer hydrogenation in a pipes-in-series flow reactor with oxo-tethered ruthenium complex-catalyzed dynamic kinetic resolution. This synthesis was accomplished without any expensive reagents, and none of the intermediates required isolation. This resulted in a robust process that has been successfully run on a production scale.

The synthesis and biological characterization of a ceramide library

A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright

Synthesis of two pairs of enantiomeric C18-sphingosines

Two pairs of enantiomeric (D-erythro, L-erythro, D-threo, L-threo) C18-sphingosines have been synthesized from Z-butene-1,4-diol utilizing Sharpless asymmetric epoxidation and a regiospecific ring-opening reaction of the resulting C4-chiral epoxide with an azide anion.

Iodocyclofunctionalization of (Z)-1-Trichloroacetimidoyloxyalk-2-enes and 3-Trichloroacetimidoyloxyalk-1-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate and (+/-)-threo-Sphinganine Triacetate

(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihidro-oxazole.From this compound, two routes were developed, either to pure (+/-)-erythro-sphinganine triacetate or to pure (+/-)-threo-sphinganine triacetate, respectively.The neutral cleavage of 4-(1-iodohexadecyl)-2-trichloromethyl-4,5,-dihydro-oxazole gave the corresponding amide which, by treatment with Amberlyst A 26 (CO3(2-) form), afforded the cis-4-hydroxymethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazole together with a minor amount of cis-2-hydroxymethyl-3-pentadecylaziridine.After hydrolysis of the oxazole and full acetylation, (+/-)-erythro-sphinganine triacetate was obtained in 70 percent yield.On the other hand, acidic cleavage of the 4-(1-iodohexadecyl)oxazole 2-amino-3-iodo-octadecan-1-ol hydrochloride, which was directly treated with Amberlyst A 26 (AcO(-) form).The product was acetylated and (+/-)-threo-sphinganine triacetate was recovered in 70 percent yield after chromatographic separation.As an alternative, 3-trichloroacetimidoyloxyoctadec-1-ene was cyclized with N-iodosuccinimide to give a 20:80 cis:trans mixture of 4-iodomethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazoles.After ring cleavage, the corresponding ring-opened hydrochlorides were obtained.The mixture was then treated with Amberlyst A 26 (AcO(-) form) and the product was directly acetylated.After silica gel chromatography, (+/-)-threo-sphinganine triacetate and (+/-)-erithro-sphinganine triacete were obtained in good yield, in the ratio 80:20.

Iodocyclofunctionalization of (E)-1-Trichloroacetimidoalk-2-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate

From the iodocyclization of (E)-1-trichloroacetimido-octadec-2-ene, 5-iodo-4-pentadecyl-2-trichloromethyl-5,6-dihydro-4H-oxazine was unexpectedly obtained, whose structue was assigned from i.r. and (1)H n.m.r. spectra.The stereostructure of this oxazine was further confirmed by chemical evidence: thus, the compound was hydrolysed on silica gel to give 2-iodo-3-trichloroacetimido-octadecan-1-ol, and successive treatment with Amberlyst A 26 (CO3(2-) form) yielded cis-5-hydroxymethyl-4-pentadecyl-4,5-dihydro-oxazole, whose configuration was determined by (1)H n.m.r. data.Acidic hydrolysis of this oxazole and acetylation led to erythro-3-aminno-octadecane-1,2-diol triacetate.To ascertain definitively the structure of this triacetate, 3-trichloroacetamido-octadec-1-ene was cyclized, to yield 5-iodomethyl-4-pentadecyl-4,5-dihydro-oxazole as a 45:55 cis:trans mixture.After hydrolysis of the cis-isomer, treatment with Amberlyst A 26 (AcO(1-) form), and full acetylation, the aforementioned erythro-triacetate was obtained.Confirming the unequivocal assignment of the stereostructure of 5-iodo-4-pentadecyl-2-trichloromethyl-5,6-dihydro-4H-oxazine, its acidic cleavage gave 3-amino-1-iodo-octadecan-2-ol hydrochloride.By treatment of this salt with Amberlyst A 26 (AcO(1-) form), full acetylation of the product afforded (+/-)-erythro-sphinganine triacetate in good yield, contaminated with a minor amount of the regioisomeric 3-amino-octadecanediol-triacetate.