80860-56-6

Upstream product

• 75336-65-1 methyl 2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranuorate 
• 545-06-2 trichloroacetonitrile 
• 1400906-88-8 1-p-tolyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranuronic acid 
• 479252-05-6 ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol 

Downstream Products

• 55610-74-7 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-62-4 C₅₇H₇₈O₇ 
• 80860-61-3 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 82300-57-0 Dibutyl(methyl-2,3,4-tri-O-benzyl-β-D-glucopyranuronatosyl)phosphat 
• 80860-60-2 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-58-8 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-62-4 C₅₇H₇₈O₇ 
• 80860-58-8 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-61-3 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 82300-56-9 Dibenzyl(methyl-2,3,4-tri-O-benzyl-β-D-glucopyranuronatosyl)phosphat 
• 75336-69-5 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-57-7 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

PNEUMOCOCCAL POLYSACCHARIDE-PROTEIN CONJUGATE COMPOSITION

The present invention relates to immunogenic compositions comprising a conjugate of a saccharide from Streptococcus pneumoniae serotype 8 and a carrier protein, and a mixture consisting of capsular polysaccharides from Streptococcus pneumoniae serotypes 1, 3, 4, 5, 6A, 6B, 7F, 9V, 14, 18C, 19A, 19F and 23F individually conjugated to CRM197 carrier protein, or a mixture consisting of capsular polysaccharides from Streptococcus pneumoniae serotypes 1, 4, 5, 6B, 7F, 9V, 14, 18C, 19F and 23F individually conjugated to a carrier protein, wherein the capsular polysaccharides from Streptococcus pneumoniae serotypes 1, 4, 5, 6B, 7F, 9V, 14, and 23F are individually conjugated to protein D, the capsular polysaccharide from Streptococcus pneumoniae serotype 18C is conjugated to tetanus toxoid and the capsular polysaccharide from Streptococcus pneumoniae serotype 19F is conjugated to diphtheria toxoid. Said compositions are useful for the prevention and/or treatment of diseases caused by Streptococcus pneumoniae.

Comparison of Several Glucuronate Glycosyl Donors

Methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D- glucopyranuronate (12), methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]- α-D-glucopyranuronate (14), methyl 2-O-acetyl-3,4-di-O-benzyl-α-D- glucopyranuronate bromide (15), methyl (2-O-acetyl-3,4-di-O-benzyl-α-D- glucopyranosyl)uronate trichloroacetimidate (17), and methyl (2,3,4-tri-O-benzyl-α/β-D-glucopyranosyl)uronate trichloroacetimidate (30) were synthesized and used as glycosyl donors. Glycosylation reactions of 12 with (5-R)-2,3,4,5-tetrahydro-5-trityloxymethyl-2- furanone (32) and 14,15,17 with the corresponding (5-R)-2,3,4,5-tetrahydro-5- hydroxymethyl-2-furanone (31) provided the exclusively β-linked glucuronide 33 in 69%, 28%, 45%, and 71% yield, respectively. The coupling of donor 30 with acceptor 31 furnished the glucuronated lactone 35 in 70% yield with a surprisingly high content (20%) of the undesired α-linked sugar residue. The structure of 33 was proved by NMR and X-ray diffraction studies. In a model reaction a complete deprotection procedure of the glucuronic acid lactone conjugation was demonstrated.