35301-25-8

Basic information

• Product Name: N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadecyl)-acetamide
• CAS NO: 35301-25-8
• Molecular Weight: 343.55
• Mol File: 35301-25-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadecyl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadecyl)-acetamide(35301-25-8)
• EPA Substance Registry System: N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadecyl)-acetamide(35301-25-8)

Safety Data

• Hazardous Substances Data: 35301-25-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 6036-86-8 (-)-L-threo-sphinganine 
• 3102-56-5 dihydrosphingosine 

Relevant articles and documents

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

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.