70834-40-1

Upstream product

• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 

Downstream Products

• 65372-01-2 2-methyl-(4-O-acetyl-3,6-di-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 
• 65730-05-4 1-propenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 74948-67-7 allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2-tetrahydropyranyl)-β-D-glucopyranoside 
• 65371-99-5 1-propenyl 2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 65730-02-1 allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 92949-52-5 allyl 2-acetamido-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 92949-53-6 allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 92949-56-9 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 114360-80-4 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 92949-54-7 Benzoic acid (2R,3R,4R,5S,6R)-2-allyloxy-3-amino-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 
• 92949-55-8 allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside 
• 275367-44-7 allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-(fluorosulfonylbenzoyl)-β-D-galactopyranoside 
• 275367-41-4 allyl 2-acetamido-2-deoxy-3,6-di-O-benzoyl-4-O-tetrahydropyranyl-β-D-galactopyranoside 
• 275367-47-0 allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-tetrahydropyranyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure

2,2'-N:3,3'-O-Tetrakis-β(1-6)-D-glucosamine disaccharide 1,4'-bis(phosphate) and its dephospho derivatives were synthesized.The bisphosphate prepared was shown to be identical with a natural biosynthetic precursor of lipid A which corresponds to the lipophilic part of lipopolysaccharide (LPS) in bacterial cell wall.The synthetic bis- and monophosphates exhibited many of typical endotoxic activities of LPS.Consequently, this work established the chemical structure of the biosynthetic precursor of lipid A and elucidated the fundamental structure required for the expression of these activities.

CHEMICAL SYNTHESIS OF PHOSPHORYLATED TETRAACYL DISACCHARIDE CORRESPONDING TO A BIOSYNTHETIC PRECURSOR OF LIPID A

A total synthesis of 2,2'-N; 3,3'-O-tetraquis-β(1-6)-D-glucosamine disaccharide 1,4'-diphosphate is described.This is the first confirmation of the fundamental structure of lipid A since the synthetic compound exhibited most of the characteristic biological activities of natural endotoxin.