160280-70-6

Upstream product

• 506-46-7 1-hexacosanoic acid 
• 202812-11-1 3,4 di-O-benzylphytosphingosine 
• 201002-42-8 C₅₁H₆₃N₃O₃ 
• 201002-48-4 C₃₇H₅₁N₃O₃ 
• 201002-41-7 (2R,3S,4R)-2-azidooctadecane-1,3,4-triol 
• 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 
• 160280-68-2 (1S,2S,3R)-2,3-Bis-benzyloxy-1-trityloxymethyl-heptadecylamine 
• 160280-65-9 (2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl methanesulfonate 
• 100-44-7 benzyl chloride 
• 202812-10-0 (2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol 
• 160280-67-1 (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol 
• 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 

Downstream Products

• 176020-22-7 (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-amino-1,3,4-octadecanetriol 
• 57-50-1 Sucrose 
• 1056025-04-7 C₆₆H₁₀₄N₂O₅ 
• 1089187-98-3 (2S,3S,4R)-3,4-di-O-benzyl-1-O-(6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-2-hexacosylamino-octadecane-1,3,4-triol 
• 1448529-93-8 (2R,3S,4R)-2-hexacosylamino-3,4-di-O-benzyloctadecanoic acid 

Relevant academic research and scientific papers

Design and synthesis of new KRN7000 analogues

Presented by CD1d protein, KRN7000, a potent synthetic α- galactosylceramide, is known to stimulate the iNKT cells to produce different bioactive cytokines. Six new KRN7000 analogues, in which the amide bond in KRN7000 is replaced with O, NH, or ester groups incorporating variation of the acyl chain, or possessing an additional four-atom linker between the galactose and phytosphingosine moiety, were designed and synthesized. The synthetic compounds were evaluated for their ability to stimulate cytokine release and the preliminary structure-activity relationships were discussed. The synthetic strategy will benefit the construction of more KRN7000 derivatives, which may contribute to cytokine profile bias.

AMINOCYCLITOL COMPOUNDS, PROCEDURE FOR THE OBTAINMENT AND USES

Aminocyclitol compounds, process for obtaining them and uses Aminocyclitol compounds and uses thereof as pharmaceutical compositions for the treatment of diseases associated with alterations in iNKT cells, more specifically autoimmune diseases, cancer, in

AMINOCYCLITOL COMPOUNDS, PROCESS FOR OBTAINING THEM AND USES

Aminocyclitol compounds and uses thereof as pharmaceutical compositions for the treatment of diseases associated with alterations in iNKT cells, more specifically autoimmune diseases, cancer, infections caused by pathogenic microorganisms or inflammatory

Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3)

Glycoceramides can activate NKT cells by binding with CD1d to produce IFN-γ, IL-4, and other cytokines. An efficient synthetic pathway for α-galactosylceramide (KRN7000) was established by coupling a protected galactose donor to a properly protected ceramide. During the investigation, it was discovered that when the ceramide was protected with benzyl groups, only β-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced α-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Galα1-3Galβ1-4Glc donor with 2-azido-sphingosine in high yield. Biological assays on the synthetic KRN7000 and iGb3 were performed using human and murine iNKT cell clones or hybridomas.

HEPATITIS C VIRUS INHIBITOR COMPRISING ALPHA-GLYCOSYLCERAMIDE AS THE ACTIVE INGREDIENT

This invention provides a growth inhibitor of human hepatitis C virus comprising, as an active ingredient, α-glycosylceramide used for patients infected with the aforementioned viruses. This inhibitor of hepatitis C virus comprises, as an active ingredien

Synthesis of D-erythro-ceramide-1-phosphoinositol and its aminoglucosylated derivative - Intermediates in GPI-anchor biosynthesis

The readily available 2,3:4,5-di-O-cyclohexylidene-D-myo-inositol derivative 3 was converted into the 1-O-unprotected D-myo-inositol derivative 6. Reaction with the phosphite derivative 7 of 3-O-tert-butyldimethylsilyl-protected ceramide furnished the target molecule D-erythro-ceramide-1-phosphoinositol (1). Reaction of O-(3,4,6-tri-O-acetyl-2-azido-β-D-glucopyranosyl)trichloroacetimidate (20) with 3 gave exclusively α(1→6)-connected glycoside 21 which was converted into the 1α-O-unprotected derivative 24. Reaction with the D-erythro-azidophytosphingosine-derived ceramide-1-phosphite derivative 17 led, after oxidation and removal of the cyanoethyl group, to protected 2-azido-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phospho-ceramide (25) which could bo fully deprotected in two steps to afford the target molecule, the ceramide derivative of 2-amino-2-deoxy-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phosphate (2).

Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylceramide, KRN7000

A practical total synthesis of (2S,3S,4A)-1-O-(α-D-galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol (KRN7000), an antitumorial and immunostimulatory glycosphingolipid derived from agelasphins, was achieved in 14 steps starting from D-lyxose in a 16% overall yield.