181583-99-3

Upstream product

• 181583-98-2 (2S,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-3-[(2R,4aR,6S,7R,8R,8aS)-8-(2-chloro-acetoxy)-2-phenyl-7-(2,2,2-trichloro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 181584-01-0 Chloro-acetic acid (2R,4aR,6R,7R,8R,8aS)-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-7-(2,2,2-trichloro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 181584-06-5 (2S,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-3-[(2R,4aR,6S,7R,8R,8aS)-8-(2-chloro-acetoxy)-2-phenyl-7-(2,2,2-trichloro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 181584-10-1 (2S,3S,4S,5R,6R)-3-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4,5-bis-benzoyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of hyaluronic acid-related tetra-, hexa-, and octa-saccharides having a methyl β-D-glucopyranosiduronic acid at the reducing end

Expeditious and stereocontrolled syntheses are reported of β-D-Glc pNAc-(1 → 4)-[β-D-Glc pA-(1 → 3)-β-D-Glc pNAc-(1 → 4)](n)-β-D-Glc pA-(l → OMe), where n = l, 2, and 3, which represent structural elements of the extracelIuIar polysaccharide hyaluronic acid. Condensation of 4,6-O-benzylidene-3-O-chloroacety l-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl trichloroacetimidate with methyl (4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate gave the disaccharide derivative 9, which was demethoxyphenylated and imidoylated to afford the pivotal disaccharide trichloroacetimidate 7. Condensation of 7 with methanol followed by O-dechloroacetylation gave the acceptor 8. Coupling of 7 with 8 gave the tetrasaccharide derivative 4. O-Dechloroacetylation of 4 followed by condensation with imidate 7 afforded hexasaccharide 5, which was transformed into octasaccharide 6 by a similar two-step procedure. Subsequent O-dechloroacetylation, transformation of the N-trichloroacetyl groups into N-acetyl, debenzylidenation, and saponification of 4-6 afforded the tetra- (1), hexa- (2), and octa-saccharide (3) derivatives in high yields, as their sodium salts.