185801-00-7

Upstream product

• 87357-67-3 (R)-3-benzyloxytetradecanoic acid 
• 183388-21-8 allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 188583-14-4 allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 912941-31-2 allyl 4,6-O-benzylidene-3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-α-D-glucopyranoside 
• 192196-09-1 6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate 
• 192196-07-9 allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 912941-36-7 benzyloxycarbonylmethyl 3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-6-O-(N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl)-α-D-glucopyranoside 
• 912941-35-6 benzyloxycarbonylmethyl 3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-6-O-(N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-D-seryl)-α-D-glucopyranoside 
• 912941-69-6 benzyloxycarbonylmethyl 3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-6-O-(N-tert-butoxycarbonyl-O⁴-benzyl-D-aspartyl)-2-deoxy-α-D-glucopyranoside 
• 912941-70-9 benzyloxycarbonylmethyl 3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-6-O-(N-tert-butoxycarbonyl-O⁴-benzyl-L-aspartyl)-2-deoxy-α-D-glucopyranoside 
• 912941-33-4 benzyloxycarbonylmethyl 4,6-O-benzylidene-3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-α-D-glucopyranoside 
• 912941-34-5 benzyloxycarbonylmethyl 3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-2-α-D-glucopyranoside 
• 912941-32-3 formylmethyl 4,6-O-benzylidene-3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-α-D-glucopyranoside 
• 185801-05-2 allyl 6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of lipid A monosaccharide analogues containing acidic amino acid: Exploring the structural basis for the endotoxic and antagonistic activities

For elucidation of the structural and conformational requirements on the endotoxic and antagonistic activity of lipid A derivatives, we designed and synthesized lipid A analogues containing acidic amino acid residues in place of the non-reducing end phosp

New efficient synthesis of a biosynthetic precursor of lipid A

A biosynthetic precursor of lipid A has been synthesized by an improved efficient method. Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the correspending trichloroacetimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yield through 13 steps from N-Troc-D-glucosamine.