25695-95-8

Basic information

• Product Name: L-THREO-SPHINGOSINE
• Synonyms: (2S,3S,4E)-2-AMINO-1,3-OCTADEC-4-ENEDIOL;(2S,3S,4E)-2-AMINOOCTADEC-4-ENE-1,3-DIOL;L-THREO-SPHINGOSINE;L-THREO-SPHINGOSINE, C18 CHAIN;(2S,3S,4E)-2-Amino-4-octadecene-1,3-diol;L-threo-C18-Sphingosine;threo-(2S,3S)-Sphingosine;L-THREO-SPHINGOSINE C-18
• CAS NO: 25695-95-8
• Molecular Formula: C₁₈H₃₇NO₂
• Molecular Weight: 299.49
• Mol File: 25695-95-8.mol

Chemical Properties

• Melting Point: 86-88 °C
• Boiling Point: 445.9±45.0 °C(Predicted)
• Appearance: /
• Density: 0.939±0.06 g/cm3(Predicted)
• PKA: 11.80±0.45(Predicted)
• CAS DataBase Reference: L-THREO-SPHINGOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-THREO-SPHINGOSINE(25695-95-8)
• EPA Substance Registry System: L-THREO-SPHINGOSINE(25695-95-8)

Safety Data

• Hazardous Substances Data: 25695-95-8(Hazardous Substances Data)

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 
• 102464-85-7 (+/-)-erythro-2-amino-3-hydroxy-octadec-4t-enoic acid ethyl ester; hydrochloride 
• 109789-11-9 rac-N-phthaloylsphingosine 
• 86120-45-8 (+/-)--4-(1-hydroxy-2-hexadecenyl)-2-oxazolidinone 
• 104826-33-7 erythro-5-amino-2,2-dimethyl-4-<(E)-pentadec-1-enyl>-1,3-dioxane 
• 94306-60-2 2-nitro-octadec-4(E)-ene-1,3-diol 

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⁾ 
• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 2482-37-3 dl-erythro-triacetylsphingosine 
• 252039-52-4 erythro-(E)-2-(stearoylamino)-4-octadecene-1,3-diol 
• 4201-58-5 rac-erythro-N-palmitoylsphingosine 
• 252039-52-4 (2R,3S)-(E)-2-(stearoylamino)-4-octadecene-1,3-diol 
• 78779-96-1 N,O,O-triacetyl-L-threo-C₁₈-sphingosine 
• 143615-69-4 (2S,3S,4E)-2-N-acetylamino-1,3-dihydroxyoctadec-4-ene 
• 189894-79-9 C6-L-threo-ceramide 
• 252039-52-4 N-((2S,3S,E)-1,3-dihydroxyoctadec-4-en-2-yl)stearamide 

Relevant articles and documents

Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine

A new enantioselective catalysis has been developed for the one-step construction of methylene-bridged chiral modules of 1,2- and 1,3-OH and/or NH function(s) from δ- or λ-OH/NHBoc-substituted allylic alcohols and H2C=O / H2C=NBoc . A protonic nucleophile, either in situ-generated CH2OH or CH2NHBoc, is intramolecularly allylated to furnish eight possible 1,2- or 1,3-O,O, -O,N, -N,O, and -N,N chiral modules equipped with an ethenyl group in high yields and enantioselectivities. The utility of this method has been demonstrated in the five-step synthesis of sphingosine.

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.

A short and efficient stereoselective synthesis of all four diastereomers of sphingosine

Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 and reduction of the free α′-amino enone derivative 7 with Zn(BH4)2.

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).