1319731-16-2

Basic information

• Product Name: (1R,2S,3S,4S,5S,6S)-2-((S)-2-amino-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethylamino)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol
• Synonyms: (1R,2S,3S,4S,5S,6S)-2-((S)-2-amino-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethylamino)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol
• CAS NO: 1319731-16-2
• Molecular Weight: 893.26
• Mol File: 1319731-16-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2S,3S,4S,5S,6S)-2-((S)-2-amino-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethylamino)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3S,4S,5S,6S)-2-((S)-2-amino-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethylamino)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol(1319731-16-2)
• EPA Substance Registry System: (1R,2S,3S,4S,5S,6S)-2-((S)-2-amino-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethylamino)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol(1319731-16-2)

Safety Data

• Hazardous Substances Data: 1319731-16-2(Hazardous Substances Data)

Upstream product

• 1319731-14-0 N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)-6-hydroxycyclohexylamino)ethyl)-2-nitrobenzenesulfonamide 
• 1319731-12-8 (1R,2S,3S,4S,5S,6S)-2-amino-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol 
• 1319731-29-7 (1R,2S,3S,4S,5S,6S)-2-azido-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)cyclohexan-1-ol 
• 1320336-58-0 (1R,2R,3S,4S,5R,6R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl )-7-oxabicyclo[4.1.0]heptane 
• 1085301-08-1 (S)-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1, 3-dioxolan-4-yl)-1-(2-nitrophenylsulfonyl)aziridine 

Downstream Products

• 1319731-10-6 N-((S)-1-((1S,2R)-1,2-dihydroxyhexadecyl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4,6-tetrahydroxy-5-hydroxymethylcyclohexylamino)ethyl)cerotamide hydrochloride 
• 1319731-41-3 N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)-6-hydroxycyclohexylamino)ethyl)cerotamide 

Relevant articles and documents

Galacto-configured aminocyclitol phytoceramides are potent in vivo invariant natural killer T cell stimulators

A new class of α-galactosylceramide (αGC) nonglycosidic analogues bearing galacto-configured aminocyclitols as sugar surrogates have been obtained. The aminocyclohexane having a hydroxyl substitution pattern similar to an α-galactoside is efficiently obtained by a sequence involving Evans aldol reaction and ring-closing metathesis with a Grubbs catalyst to give a key intermediate cyclohexene, which has been converted in galacto-aminocyclohexanes that are linked through a secondary amine to a phytoceramide lipid having a cerotyl N-acyl group. Natural Killer T (NKT) cellular assays have resulted in the identification of an active compound, HS161, which has been found to promote NKT cell expansion in vitro in a similar fashion but more weakly than αGC. This compound stimulates the release of Interferon-γ (IFNγ) and Interleukin-4 (IL-4) in iNKT cell culture but with lower potency than αGC. The activation of Invariant Natural Killer T (iNKT) cells by this compound has been confirmed in flow cytometry experiments. Remarkably, when tested in mice, HS161 selectively induces a very strong production of IFN-γ indicative of a potent Th1 cytokine profile. Overall, these data confirm the agonist activity of αGC lipid analogues having charged amino-substituted polar heads and their capacity to modulate the response arising from iNKT cell activation in vivo.