160280-66-0

Basic information

• Product Name: 3,4-Octadecanediol, 2-azido-1-(triphenylmethoxy)-, (2S,3S,4R)-
• CAS NO: 160280-66-0
• Molecular Formula: C37H51N3O3
• Molecular Weight: 585.83
• Mol File: 160280-66-0.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 3,4-Octadecanediol, 2-azido-1-(triphenylmethoxy)-, (2S,3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Octadecanediol, 2-azido-1-(triphenylmethoxy)-, (2S,3S,4R)-(160280-66-0)
• EPA Substance Registry System: 3,4-Octadecanediol, 2-azido-1-(triphenylmethoxy)-, (2S,3S,4R)-(160280-66-0)

Safety Data

• Hazardous Substances Data: 160280-66-0(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 117168-59-9 (2S,3S,4R)-2-azido-1,3,4-octadecanetriol 
• 4099-88-1 (3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol 
• 77844-50-9 (2S,3S,4R)-2-aminooctadecane-1,3,4-triol hydrochloride 
• 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 
• 160280-64-8 Methanesulfonic acid (E)-(1R,2R,3R)-2,3-dihydroxy-1-hydroxymethyl-heptadec-4-enyl ester 
• 160280-65-9 (2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl methanesulfonate 
• 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 

Downstream Products

• 160280-67-1 (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol 
• 848827-63-4 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 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 
• 1068564-82-8 1-O-trityl-phytosphingosine 
• 1384423-87-3 1-O-(α-D-galactopyranosyl)-2-(11-(3,4-dichlorophenyl)undecanoyl)amino-D-ribo-1,3,4-octadecanetriol 

Relevant articles and documents

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

A comparison of benzyl and 2-naphthylmethyl ethers as permanent hydroxyl protecting groups in the synthesis of α-galactoglycosphingolipids KRN7000 and PBS-57

Due to the interest in the biological properties of marine derived α-galactoglycosphingolipids (α-GalGSLs), a lot of work has focused on the development of their synthesis. Here we conducted the direct comparison of benzyl and 2-naphthylmethyl (Nap) ether

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.