103348-50-1

Basic information

• Product Name: (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol
• Synonyms: (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol
• CAS NO: 103348-50-1
• Molecular Weight: 429.603
• Mol File: 103348-50-1.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol(103348-50-1)
• EPA Substance Registry System: (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol(103348-50-1)

Safety Data

• Hazardous Substances Data: 103348-50-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol is used as a research compound for its potential role in the development of new pharmaceuticals. Its unique structure allows for exploration of its interactions with biological systems and the possibility of creating new drugs with specific therapeutic properties.
Used in Biological Research:
In biological research, (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol is used as a tool to study various biological processes. The presence of the azide and benzoyloxy groups may enable targeted interactions with specific biomolecules, providing insights into cellular mechanisms and potential therapeutic targets.
Further studies are necessary to fully understand the potential uses and effects of (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol, as its complex structure and functional groups present a rich area for scientific exploration and application in both pharmaceutical and biological fields.

Upstream product

• 108283-58-5 (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 112-71-0 1-Bromotetradecane 
• 471907-67-2 Benzoic acid (E)-(R)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-hexadec-2-enyl ester 
• 471907-69-4 Acetic acid (R)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-hexadec-2-ynyl ester 
• 471907-68-3 Acetic acid (S)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-hexadec-2-ynyl ester 
• 471907-65-0 (S)-(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-hexadec-2-yn-1-ol 
• 471907-64-9 (2R,3R)-1,2-O-cyclohexylidene-4-octadecyne-1,2,3-triol 
• 471907-66-1 (2R,3R,4E)-1,2-O-cyclohexylidene-4-octadecene-1,2,3-triol 
• 335595-99-8 (2S,3R,4E)-3-benzoyloxy-1-thexyldimethylsilyloxy-octadec-4-ene-2-ol 
• 98-88-4 benzoyl chloride 
• 765-13-9 pentadec-1-yne 
• 372515-93-0 1-methoxymethyl-2-azido-3-benzoyl-D-(+)-erythro-sphingosine 
• 3006-41-5 4,6-O-benzylidene-α,β-D-galactopyranose 
• 10257-28-0 D-Galactose 

Downstream Products

• 197144-04-0 Benzoic acid (E)-(R)-1-[(S)-1-octadecanoylamino-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 197144-09-5 Benzoic acid (E)-(R)-1-{(S)-2-[(2R,3R,4S,5R)-3,4-diacetoxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-1-octadecanoylamino-ethyl}-hexadec-2-enyl ester 
• 172276-01-6 (2S,3R,4E)-2-azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-4-octadecene 
• 1028795-73-4 C₇₂H₁₀₄N₄O₃₁ 
• 1290105-28-0 2-azido-3-O-benzoyl-D-erythro-sphingosine-1-yl 2,3,6-tri-O-benzoyl-4-O-[2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-4,6-O-di-tert-butylsilanediyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside 
• 2238-90-6 psychosine 
• 1670-26-4 sphingosylphosphorylcholine 
• 206857-30-9 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-p-methoxybenzyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene 
• 206857-29-6 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-p-methoxybenzyl-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene 
• 206857-88-7 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene 
• 206857-07-0 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene 
• 206857-67-2 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene 
• 206857-66-1 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-α-D-galactopyranosyloxy]-4-octadecene 
• 206856-96-4 (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene 

Relevant articles and documents

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

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

An Improved, Versatile, and Easily Scalable Synthesis of Sphingomyelins: Application to Stable Isotope Labeling

With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3- O -benzoylsphingos

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

3-O-SULFO-GALACTOSYLCERAMIDE ANALOGS AS ACTIVATORS OF TYPE II NKT CELLS AND USES THEREOF

Disclosed is a compound of the formula (I) or (II): wherein a f are as described herein. The compounds are useful in the activation of Type II NKT cells and in treating cancer.

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

Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies

An α-l-rhamnosyl ceramide (1, α-l-RhaCer) has been prepared that was recognized by anti-l-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-l-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from d-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-l-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-l-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-l-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-l-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-l-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.

A concise synthesis of globotriaosylsphingosine

Globotriaosylsphingosine (lysoCTH) is produced in the cell by deacylation of the globo-sphingolipid globotriaosylceramide. The latter compound is the major storage material encountered in Fabry patients, an inherited lysosomal storage disorder characteriz

Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alco

The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog

The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.