202812-10-0

Basic information

• Product Name: 1-Octadecanol, 2-azido-3,4-bis(phenylmethoxy)-, (2S,3S,4R)-
• Synonyms: 1-Octadecanol,2-azido-3,4-bis(phenylmethoxy)-,(2S,3S,4R)
• CAS NO: 202812-10-0
• Molecular Formula: C32H49N3O3
• Molecular Weight: 523.759
• Mol File: 202812-10-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-Octadecanol, 2-azido-3,4-bis(phenylmethoxy)-, (2S,3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Octadecanol, 2-azido-3,4-bis(phenylmethoxy)-, (2S,3S,4R)-(202812-10-0)
• EPA Substance Registry System: 1-Octadecanol, 2-azido-3,4-bis(phenylmethoxy)-, (2S,3S,4R)-(202812-10-0)

Safety Data

• Hazardous Substances Data: 202812-10-0(Hazardous Substances Data)

Usage

Class

Long-chain fatty alcohols

Chemical structure

A long hydrocarbon chain with a hydroxyl group at one end and azido and bis(phenylmethoxy) groups at the other end

Chiral molecule

The molecule has a specific spatial arrangement of its atoms

Configuration

(2S,3S,4R) indicating the positions of substituent groups around the chiral carbon atoms within the molecule

Potential applications

Pharmaceutical, materials science, and organic synthesis industries

Note

Further research and testing are required to determine specific uses and effects.

Upstream product

• 4099-88-1 (3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol 
• 412031-49-3 (2R,3S,4R)-3,4-Bis-benzyloxy-1-triisopropylsilanyloxy-octadecan-2-ol 
• 600168-67-0 2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol 
• 600168-66-9 3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,2,3,4-tetraol 
• 160280-62-6 3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadec-5-en-1,2,3,4-tetraol 
• 100-39-0 benzyl bromide 
• 853013-15-7 (2R,3S,4R)-3,4-di-O-benzyl-1,2,3,4-octadecanetetrol 
• 160280-66-0 (2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol 
• 117168-59-9 (2S,3S,4R)-2-azido-1,3,4-octadecanetriol 
• 554-62-1 D-ribo-phytosphingosine 
• 412031-50-6 ((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-triisopropyl-silane 
• 160280-67-1 (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol 
• 201002-42-8 C₅₁H₆₃N₃O₃ 
• 201002-48-4 C₃₇H₅₁N₃O₃ 

Downstream Products

• 848827-40-7 (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran 
• 1384423-87-3 1-O-(α-D-galactopyranosyl)-2-(11-(3,4-dichlorophenyl)undecanoyl)amino-D-ribo-1,3,4-octadecanetriol 
• 1448529-93-8 (2R,3S,4R)-2-hexacosylamino-3,4-di-O-benzyloctadecanoic acid 
• 951767-71-8 2-azido-3,4-di-O-benzyl-1-O-(2,3-di-O-benzyloxyl-4,6-O-benzyllidene-α-D-galactopyranosyl)-D-ribooctadecane-1,3,4-triol 
• 412031-51-7 Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester 
• 202812-11-1 3,4 di-O-benzylphytosphingosine 

Relevant articles and documents

Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain

A novel series of CD1d ligand α-galactosylceramides (α-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of α-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid–protein interactions in KRN7000/CD1d complexes.

Synthesis and Evaluation of Acyl-Chain- and Galactose-6′′-Modified Analogues of α-GalCer for NKT Cell Activation

α-GalCer is an immunostimulating glycolipid that binds to CD1d molecules and activates invariant natural killer T (iNKT) cells. Here we report a scaled-up synthesis of α-GalCer analogues with modifications in the acyl side chain and/or at the galactose 6′′-position, together with their evaluation in vitro and in vivo. Analogues containing 11-phenylundecanoyl acyl side chains with aromatic substitutions (14, 16-21) and Gal-6′′-phenylacetamide-substituted α-GalCer analogues bearing p-nitro- (32), p-tert-butyl (34), or o-, m-, or p-methyl groups (40-42) displayed higher IFN-γ/IL-4 secretion ratios than α-GalCer in vitro. In mice, compound 16, with an 11-(3,4-difluorophenyl)undecanoyl acyl chain, induced significant proliferation of NK and DC cells, which should be beneficial in killing tumors and priming the immune response. These new glycolipids might prove useful as adjuvants or anticancer agents.

Introduction of aromatic group on 4′-OH of α-GalCer manipulated NKT cell cytokine production

The glycosphingolipid α-GalCer has been found to influence mammalian immune system significantly through the natural killer T cells. Unfortunately, the pre-clinical and clinical studies revealed several critical disadvantages that prevented the therapeutic application of α-GalCer in treating cancer and other diseases. Recently, the detailed illustration of the CD1d/α-GalCer/NKT TCR complex crystal structural, together with other latest structural and biological understanding on glycolipid ligands and NKT cells, provided a new platform for developing novel glycolipid ligands with optimized therapeutic effects. Here, we designed a series of novel aromatic group substituted α-GalCer analogues. The biological activity of these analogues was characterized and the results showed the unique substitution group manipulated the immune responses of NKT cells. Computer modeling and simulation study indicated the analogues had unique binding mode when forming CD1d/glycolipid/NKT TCR complex, comparing to original α-GalCer.