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
• Article Data: 10

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 
• 18696-97-4 1,1-diethoxy-hexadec-2-yne 
• 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 

Downstream Products

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 2482-37-3 dl-threo-triacetylsphingosine 
• 2482-37-3 dl-erythro-triacetylsphingosine 
• 16170-10-8 DL-threo-1,3-Dihydroxy-2-myristoylamino-trans-octadecen-⁽⁴⁾ 
• 252039-52-4 erythro-(E)-2-(stearoylamino)-4-octadecene-1,3-diol 
• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 78779-96-1 N,O,O-triacetyl-L-threo-C₁₈-sphingosine 
• 4201-58-5 rac-erythro-N-palmitoylsphingosine 
• 252039-52-4 (2R,3S)-(E)-2-(stearoylamino)-4-octadecene-1,3-diol 
• 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 
• 928302-15-2 2-azido-1-(tert-butyldiphenylsilanyloxy)-L-threo-sphingosine 
• 928302-16-3 2-azido-3-benzoyl-1-(tert-butyldiphenylsilyloxy)-L-threo-sphingosine 

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.

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.

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.