117168-59-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S,4R)-2-Azido-1,3,4-octadecanetriol is used as a chiral building block for the synthesis of complex organic molecules and pharmaceutical compounds. Its unique stereochemistry and azide functionality allow for the development of innovative drugs with improved efficacy and selectivity.
Used in Immunology Research:
(2S,3S,4R)-2-Azido-1,3,4-octadecanetriol is used as a photo-crosslinking agent to control immune activity with light. This property enables researchers to study the immunostimulatory activity of α-galactosylceramide and other immune modulators, providing valuable insights into the regulation of immune responses.
Used in Materials Science:
(2S,3S,4R)-2-Azido-1,3,4-octadecanetriol is used as a precursor for the synthesis of functional polymers and materials with tailored properties. Its azide group can be utilized in click chemistry reactions, allowing for the efficient and selective formation of complex polymeric structures with potential applications in various fields, such as drug delivery, tissue engineering, and nanotechnology.

InChI:InChI=1/C18H37N3O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(23)18(24)16(15-22)20-21-19/h16-18,22-24H,2-15H2,1H3/t16-,17+,18-/m0/s1

Upstream product

• 117168-58-8 2-azido-1,3-O-benzylidene-D-ribo-1,3,4-octadecanetriol 
• 161459-73-0 (4S,5S)-5-Azido-4-((R)-1-methoxymethoxy-pentadecyl)-2,2-dimethyl-[1,3]dioxane 
• 160280-65-9 (2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl methanesulfonate 
• 164385-82-4 (2S,3S,4R)-1,3,4-tri-O-acetyl-2-azido-1,3,4-octadecanetriol 
• 554-62-1 D-ribo-phytosphingosine 
• 600168-67-0 2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol 
• 4099-88-1 (3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol 
• 532-20-7 D-lyxose 
• 160280-62-6 3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadec-5-en-1,2,3,4-tetraol 
• 600168-66-9 3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,2,3,4-tetraol 
• 117168-66-8 (2S,4R,5R)-4-[(R)-1-hydroxypentadecyl]-2-phenyl-1,3-dioxan-5-yl methanesulfonate 
• 160280-64-8 Methanesulfonic acid (E)-(1R,2R,3R)-2,3-dihydroxy-1-hydroxymethyl-heptadec-4-enyl ester 
• 160280-63-7 Methanesulfonic acid (R)-1-[(4R,5R)-2,2-dimethyl-5-((E)-tetradec-1-enyl)-[1,3]dioxolan-4-yl]-2-trityloxy-ethyl ester 
• 3855-45-6 triflic azide 

Downstream Products

• 160280-66-0 (2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol 
• 303752-86-5 (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol 
• 916159-68-7 (2S,3S,4R)-2-azido-1-(tert-butyldiphenylsilyloxy)octadecane-3,4-diol 
• 916159-70-1 (2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol 
• 916159-71-2 (2S,3S,4S)-2-azido-1-(tert-butyldiphenylsilyloxy)-4-iodooctadecan-3-ol 
• 916159-69-8 [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane 
• 928634-52-0 (4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 103348-49-8 2-azido-sphingosine 
• 1068564-70-4 (2S,3S,4R)-2-azido-1-benzyloxyoctadecane-3,4-diol 
• 1068564-93-1 (2S,3S,4R)-2-azido-1,3-di(benzyloxy)octadecan-4-ol 
• 129779-76-6 (2S,3S,4R)-1,3,4-tri-O-benzyl-2-azido-1,3,4-octadecanetriol 
• 1256376-20-1 (2S,3S,4R)-2-azido-1,3,4-tri-tert-butyldimethylsilyloxy-1,3,4-octadecanetriol 
• 1365757-18-1 N-((2R,3S,4R)-1-(cyclohexylthio)-3,4-isopropilidenedioxyoctadecan-2-yl)octanamide 

Relevant academic research and scientific papers

Synthesis of ganglioside Hp-s1

A simple protocol for the synthesis of a ganglioside Hp-s1 (1) starting from commercially available phytosphingosine, sialic acid, and d-glucose is described. This synthesis involved a glycosylation reaction of a phytosphingosine derived acceptor with a h

Chemoenzymatic synthesis and biological evaluation of ganglioside GM3 and lyso-GM3 as potential agents for cancer therapy

A highly efficient chemoenzymatic method for synthesizing ganglioside GM3 and lyso-GM3 was reported here. Enzymatic extension of the chemically synthesized lactosyl sphingosine using efficient one-pot multienzyme (OPME) reaction allowed glycosylation to b

GLYCOLIPID CONTROLLABLE OF IMMUNE ACTIVITY WITH LIGHT

PROBLEM TO BE SOLVED: To provide means of improving immunostimulation activity of α-galactosylceramide. SOLUTION: The invention provides a compound represented by the general formula (I) in the figure, where Ar represents an aryl group that may be substituted with substituents such as a phenyl group, or a heteroaryl group that may be substituted with substituents, and n represents an integer from 4 to 12. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Ganglioside GM3 and/or analogue thereof, synthesis method and application of ganglioside GM3 and/or analogue thereof

The invention relates to a method for synthesizing ganglioside GM3 and/or an analogue thereof. The method includes the following steps: (1) selecting a lactose donor represented by a general formula Iand/or an analogue thereof and selecting a sphingosine

A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as phytosphingosine 3,4-diol protecting group

A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected phytosphingosine is reported here. The conversion of the phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cl

A rapid synthesis of sphingosine from phytosphingosine

A simple and efficient protocol for the synthesis of a sphingosine starting from cost-effective phytosphingosine has been described. Two alternative synthetic pathway have been disclosed based on the use of two different kinds of protective groups for the protection of the amino group in the phytosphingosine. The protected phytosphingosine was subsequently transformed into sphingosine in 5 steps i.e. protection of the amine group, protection of 1,3-diol, leaving group insertion, elimination, and one-pot deprotection.

Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

A highly efficient streamlined chemoenzymatic strategy for total synthesis of four prioritized ganglioside cancer antigens GD2, GD3, fucosyl GM1, and GM3 from commercially available lactose and phytosphingosine is demonstrated. Lactosyl sphingosine (LacβS

Efficient Divergent Synthesis of New Immunostimulant 4″-Modified α-Galactosylceramide Analogues

A synthesis strategy for the swift generation of 4″-modified α-galactosylceramide (α-GalCer) analogues is described, establishing a chemical platform to comprehensively investigate the structure-activity relationships (SAR) of this understudied glycolipid

Alpha-GalCer phosphate compounds with immunocompetence and synthesis method thereof

The invention discloses alpha-GalCer phosphate compounds with immunocompetence and a synthesis method thereof, and belongs to the technical field of organic synthesis. The invention is technically characterized in that: the alpha-GalCer phosphate compound

Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc4βCer

A highly efficient chemoenzymatic method for synthesizing glycosphingolipids using α-Gal pentasaccharyl ceramide as an example is reported here. Enzymatic extension of the chemically synthesized lactosyl sphingosine using efficient sequential one-pot mult