185801-05-2

Upstream product

• 183388-21-8 allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 188583-14-4 allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 185801-00-7 allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 

Downstream Products

• 927175-32-4 allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-((R)-3-benzyloxytetradecanoyl)-2-deoxy-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 927175-37-9 allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-((R)-3-hydroxytetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 927175-38-0 allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarboylamino)-α-D-glucopyranoside 
• 927175-40-4 C₅₅H₈₀Cl₆N₂O₁₂ 
• 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 

Relevant academic research and scientific papers

Synthesis and biological activities of biscarboxymethyl lipid A analogues

Biscarboxymethyl analogues of Escherichia coli lipid A and the biosynthetic precursor-type lipid A were synthesized in order to elucidate the role of the acidic functional groups in the biological activity. Both analogues showed respective activities simi

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.