6036-75-5

Usage

Uses

Used in Pharmaceutical Industry:
L-ERYTHRO-SPHINGOSINE is used as a therapeutic agent for the treatment of various diseases, including cancer, neurodegenerative disorders, and cardiovascular disease. Its role in cell growth, differentiation, and apoptosis, as well as its involvement in various cellular processes, makes it a promising candidate for drug development.
Used in Research:
L-ERYTHRO-SPHINGOSINE is used as a research tool to study the role of sphingolipids in cellular processes and disease mechanisms. Its involvement in cell proliferation, migration, and inflammation, as well as its link to various diseases, makes it an important target for research in cell biology, biochemistry, and pharmacology.
Used in Drug Development:
L-ERYTHRO-SPHINGOSINE is used as a target for the development of new drugs and therapies. Its role in various disease processes and its involvement in cellular processes make it a valuable target for the development of drugs that can modulate its activity and potentially treat or prevent diseases.
Used in Cosmetics Industry:
L-ERYTHRO-SPHINGOSINE is used as an ingredient in cosmetics and skincare products for its potential benefits to skin health. Its role in cell growth, differentiation, and apoptosis may contribute to improved skin hydration, elasticity, and overall skin health.
Used in Food Industry:
L-ERYTHRO-SPHINGOSINE is used as a functional ingredient in certain food products due to its potential health benefits. Its role in various cellular processes and its link to disease prevention may contribute to the development of functional foods and beverages with health-promoting properties.

InChI:InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m1/s1

Upstream product

• 2733-33-7 (+/-)-threo-2-amino-octadec-4-yne-1,3-diol 
• 96040-13-0 2-nitro-4-octadecine-1,3-diol 
• 51534-40-8 2-Hexadecynal 
• 114697-01-7 (+/-)-N-(4c-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5c-yl)-acetamide 
• 94676-99-0 N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 86120-45-8 (+/-)--4-(1-hydroxy-2-hexadecenyl)-2-oxazolidinone 
• 2733-33-7 (+/-)-erythro-2-amino-octadec-4-yne-1,3-diol 
• 81819-45-6 (Z)-(2S,3S)-2-Amino-3-hydroxy-octadec-4-enoic acid 
• 94375-81-2 (+/-)-erythro-2-nitro-octadec-4-yne-1,3-diol 
• 109789-11-9 rac-N-phthaloylsphingosine 
• 86120-45-8 (+/-)--4-(1-hydroxy-2-hexadecenyl)-2-oxazolidinone 
• 93255-83-5 (2E,4E)-octadeca-2,4-dien-1-ol 
• 18696-97-4 1,1-diethoxy-hexadec-2-yne 
• 102464-85-7 (+/-)-erythro-2-amino-3-hydroxy-octadec-4t-enoic acid ethyl ester; hydrochloride 

Downstream Products

• 2482-37-3 dl-threo-triacetylsphingosine 
• 16170-10-8 DL-threo-1,3-Dihydroxy-2-myristoylamino-trans-octadecen-⁽⁴⁾ 
• 17673-67-5 DL-threo-1-(Triphenylmethoxy)-2-myristoylamino-3-hydroxy-trans-octadecen-⁽⁴⁾ 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 2482-37-3 dl-erythro-triacetylsphingosine 
• 4201-58-5 rac-erythro-N-palmitoylsphingosine 
• 252039-52-4 (2R,3S)-(E)-2-(stearoylamino)-4-octadecene-1,3-diol 
• 609812-03-5 tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate 
• 189894-79-9 Ceramide C6 
• 175892-44-1 D-erythro N-octanoylsphingosine 
• 150338-90-2 (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol 

Relevant academic research and scientific papers

Chemo-, regio-, and stereoselective silver-catalyzed aziridination of dienes: Scope, mechanistic studies, and ring-opening reactions

Silver complexes bearing trispyrazolylborate ligands (Tpx) catalyze the aziridination of 2,4-diene-1-ols in a chemo-, regio-, and stereoselective manner to give vinylaziridines in high yields by means of the metal-mediated transfer of NTs (Ts = p-toluensulfonyl) units from PhI=NTs. The preferential aziridination occurs at the double bond neighboring to the hydroxyl end in ca. 9:1 ratios that assessed a very high degree of regioselectivity. The reaction with the silver-based catalysts proceeds in a stereospecific manner, i.e., the initial configuration of the C=C bond is maintained in the aziridine product (cis or trans). The degree of regioselectivity was explained with the aid of DFT studies, where the directing effect of the OH group of 2,4-diene-1-ols plays a key role. Effective strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent formation of β-amino alcohols have also been developed.

Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

The reaction of dienyl carbamates with PhI(OR)2 in the presence of rhodium catalysts affords vinyl aziridines which are in situ regio- and stereoselectively opened to afford oxyamination products resulting from a selective SN2 (Rh2(OAc)4/PhI(OPiv)2) or SN2′ (Rh2(OPiv)4/PhI(OAc) 2) opening. The scope and limitations of this tandem process are described.

Efficient silver-catalyzed regio- and stereospecific aziridination of dienes

Nitrene transfer: Unsymmetric dienes bearing a terminal hydroxy group can be regio- and stereospecifically converted into vinylaziridines upon nitrene transfer from PhINTs using a silver-based catalyst. Stoichiometric mixtures of dienes and PhINTs were employed at low catalyst loadings (0.5□%; see scheme). The method has been applied to the synthesis of (±)-sphingosine and gave good yields in a three-step procedure. Ts=4-toluenesulfonyl.

Synthesis of D/L-erythro-Sphingosine Using a Tethered Aminohydroxylation Reaction as the Key Step

A diastereoselective synthesis of racemic D/L-erythro- sphingosine is described. The approach involves employing tethered aminohydroxylation (TA) to introduce the 2-amino and 3- hydroxy functions with required stereochemistry. Georg Thieme Verlag Stuttgart.

Lipase-catalyzed enantiomeric resolution of ceramides 1

Lipase-catalyzed enantiomeric kinetic resolution of ceramides related to C16-sphinganine and C18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythroC16-sphinganine were acetylated, and several kinds of lipases were screened for the hydrolysis of this substrate. Among them, a Burkholderia cepacia lipase (SC lipase A, Sumitomo Chemical Co., Ltd.) showed the highest reactivity and enantioselectivity. The rate of hydrolysis and selectivity were greatly affected by some additives. Especially, the combined use of a detergent, Triton X-100, and the solid support, Florisil, for immobilization showed the highest enantioselectivity (E = ca. 170), although the reaction rate turned low. Introduction of a double bond into the substrate (N-stearoyl-erythro-Cis-sphingenine) also retarded the hydrolysis. By utilizing the preferential hydrolysis of the acetate on the primary hydroxy group, another advantageous feature of this enzyme-catalyzed reaction, the resulting product could directly be used as the glycosyl acceptor for cerebroside synthesis.

A New Route to Racemic erythro-Sphingosine and Ceramides. The 1,2-versus 1,4-Addition Reaction of Hexadec-2-enal with 2-Nitroethanol

The reaction of hexadec-2-enal (5) with 2-nitroethanol (3) in triethylamine gave the 1,2-adducts (8) and (9), while the reaction in methanol-potassium carbonate gave the Michael adducts (6) and (7).Epimerization of the threo-acetonide (10) smoothly gave the erythro-acetonide (11), which gave the amino acetonide (12) on reduction.Phthaloylation, deacetalization, and deprotection of compound (12) gave rac-erythro-sphingosine (1).On the other hand, acylation and deacetalization of compound (12) gave the ceramide (16).