114275-39-7

Basic information

• Product Name: (2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL
• Synonyms: (2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL;(2R,3R,4E)-1,3-O-benzylidene-4-*octadecene-1,2,3-;(2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECEN E-1,2,3-TR
• CAS NO: 114275-39-7
• Molecular Formula: C₂₅H₄₀O₃
• Molecular Weight: 388.58
• Product Categories: Lipids;Other Lipid Related Products;Other Lipids&Mixtures of Lipids
• Mol File: 114275-39-7.mol

Chemical Properties

• Boiling Point: 499°C at 760 mmHg
• Flash Point: 255.6°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 8.89E-11mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: (2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL(114275-39-7)
• EPA Substance Registry System: (2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL(114275-39-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 114275-39-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure, including the benzylidene group and the chiral centers, allows for selective reactions and the formation of complex molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
(2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL is used as a building block in the development of pharmaceutical compounds. Its structural features, such as the benzylidene group and the hydroxyl groups, can be exploited to design new drugs with specific biological activities. The chiral centers also provide opportunities for the synthesis of enantiomerically pure compounds, which can have improved pharmacological properties and reduced side effects.
Used in Biological Systems:
(2R,3R,4E)-1,3-O-BENZYLIDENE-4-OCTADECENE-1,2,3-TRIOL may have potential applications in biological systems due to its structural features. The presence of the benzylidene group and the hydroxyl groups can enable interactions with biological molecules, such as proteins and nucleic acids. This can lead to the development of new tools and reagents for biological research and the discovery of novel bioactive compounds with potential therapeutic applications.

InChI:InChI=1/C25H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-24-23(26)21-27-25(28-24)22-18-15-14-16-19-22/h14-20,23-26H,2-13,21H2,1H3/b20-17+/t23-,24-,25+/m1/s1

Upstream product

• 117112-62-6 (2R,3R)-cis-1,3-O-benzylidene-1,2,3-octadec-4-enetriol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 99274-32-5 2,4-O-benzylidene-D-threose 
• 96854-01-2 triphenylphosphoniotetradecylid 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 121998-84-3 (2R,3R,4E)-octadec-4-ene-1,2,3-triol 
• 432038-19-2 (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol 
• 331456-63-4 1,5-Anhydro-3,4-bis-O-(tert-butyldimethylsilyl)-2-deoxy-1-phenylsulfonyl-D-threo-pent-1-enitol 
• 331456-61-2 Phenyl 2,3,4-tris-O-(tert-butyldimethylsilyl)-1-thio-β-D-xylopyranoside 
• 331456-62-3 2,3,4-Tris-O-(tert-butyldimethylsilyl)-β-D-xylopyranosyl phenyl sulfone 
• 432038-16-9 6-benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran 
• 432038-17-0 5-(tert-butyl-dimethyl-silanyl)-2-(tert-butyl-dimethyl-silanyloxy)-octadec-4-ene-1,3-diol 
• 432038-18-1 (2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(Z)-2-(tert-butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxane 
• 112-71-0 1-Bromotetradecane 

Downstream Products

• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 108283-57-4 (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 52050-17-6 Glucosylsphingosine 
• 117112-63-7 (2S,3R,4E)-2-amino-1,3-benzylidene-4-octadecene-1,3-diol 
• 116447-99-5 (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 74365-77-8 glucosylceramide 
• 108283-58-5 (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 108283-59-6 (2S,3R,4E)-2',3',4',6'-tetraacetyl-β-D-glucopyranosyl-(1'<->1)-2-azido-3-benzoyl-4-octadecene-1,3-diol 
• 114299-64-8 (2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol 
• 114275-41-1 (2S,3R,4E)-2-Azido-1-(pivaloyloxy)-4-octadecen-3-ol 
• 114275-42-2 (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-1-(pivaloyloxy)-4-octadecen 
• 114299-45-5 (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-1-(triphenylmethyloxy)-4-octadecen 

Relevant articles and documents

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

4,5-Cis Unsaturated α-GalCer Analogues Distinctly Lead to CD1d-Mediated Th1-Biased NKT Cell Responses

The total synthesis of 4,5-cis unsaturated α-GalCer analogues was achieved, and their immune-response altering activity was assessed in vitro as well as in vivo in mice. Using glycosyl iodide as a glycosyl donor, construction of the sphingosine unit was shortened by four steps and single α-stereoselectivity was achieved in good yield (67%). With regard to the therapeutic use of α-GalCer, the novel analogues (1b and 1c) distinctly induced a Th1-biased cytokine response, avoiding induction of a contradictory response and overstimulation.

Synthesis of D-erythro-sphingosine and D-erythro-ceramide.

A 1,2-metallate rearrangment of a higher order cuprate derived from an alpha-lithiated xylal derivative and tridecyllithium is the key step in a synthesis of D-erythro-sphingosine and ceramide. A convenient method for preparing alpha-lithiated glycals from alpha-phenylsulfinyl glycals is also described.

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.

An efficient stereoselective synthesis of sphingosine

A stereocontrolled synthesis of D-(+)-erythro-sphingosine (1), starting from D-xylose as chiral pool material and employing the addition-fragmentation reaction of tosyl hydrazone of 2,3:4,5-di-O-isopropylidene-D-xylose as a key step for the chain extension with concomitant trans-selective C=C bond formation, is described.

SYNTHESES OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID AND PHOSPHONOSPHINGOGLYCOLIPID FOUND IN MARINE ORGANISM VIA A COMMON PRECURSOR

D-Erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable hydrogenated lipids in a non-photosynthetic marine diatom, Nitzschia alba, and (2S,3R)-N-palmitoyl-1-O--β-D-galactopyranosyl>-D-sphingosine, found in marine snail Turbo cornutus were synthesized via a common precursor (10) starting from galactose.

SYNTHESIS OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID

New D-erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable lipids in a non-photosynthetic marine diatom Nitzschia alba, was synthesized from galactose as a chiral precursor using the Hanessian-Hullar reaction as the key step in the

Synthesis of Sphingosines, 4. - Synthesis of erythro-Sphingosines via Their Azido Derivatives

The 2,4-O-protected D-threoses 3a and 3b were obtained from D-galactose and D-xylose, respectively, in two-step procedures.Wittig reaction in the presence of an excess of lithium bromide afforded the trans-enetriols 4aA, 4aB, and 4bA.Triflate activation of the unprotected 2-hydroxy group, azide group introduction, and cleavage of the O-protective groups yielded the azidosphingosines 6A,B which provide after azide group reduction the D-erythro-sphingosines 7A,B.For the glycosphingolipid synthesis through azidosphingosine glycosylation, compound 6A was transformed by 1-O tritylation, 3-O protection, and subsequent 1-O detritylation into the 3-O-protected azidosphingosines 11α-11γ.

SYNTHESIS OF D-ERYTHRO-SPHINGOSINES

2,4-Di-O-protected D-threose, readily available from D-galactose, is a versatile intermediate for D-erythro-sphingosine syntheses via trans-selective Wittig reaction, azide introduction at the unprotected hydroxylic group, and subsequent azide reduction.