93125-77-0

Upstream product

• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 1826-67-1 vinyl magnesium bromide 
• 1119-22-8 divinyl zinc 
• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 1072440-23-3 (3S,4R,5S,6R)-4,5,7-tris(benzyloxy)-6-(tert-butyldimethylsilyloxy)hept-1-en-3-ol 

Downstream Products

• 160318-52-5 (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol 
• 863028-32-4 methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate 
• 863028-36-8 benzyl (2S,5S,6R,7R,8R,E)-6,7,9-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-5,8-dihydroxynon-3-enoate 
• 1072440-18-6 (S)-((2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-hydroxyhept-6-en-2-yl) 2-(tert-butoxycarbonylamino)pent-4-enoate 
• 1072440-16-4 (2R)-methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-2-(tert-butoxycarbonylamino)butanoate 
• 1442044-34-9 C₃₇H₄₅NO₉ 
• 1442044-21-4 (S)-methyl 4-((2S,3S,4R,5R,6R)-4,5-di(benzyloxy)-6-((benzyloxy)-methyl)-3-hydroxytetrahydro-2H-pyran-2yl)-2-((tert-butoxycarbonyl)amino)butanoate 
• 1442044-28-1 (S)-methyl 4-((2S,3S,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2yl)-2-((tert-butoxycarbonyl)amino)butanoate 
• 1072440-17-5 tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate 
• 1072440-22-2 (2S,6S,7R,8R,9R,Z)-methyl 7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate 
• 180323-16-4 (2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene 
• 162239-07-8 1-deoxy-1-α-ethenyl-2,3,5-tri-O-benzyl-L-xylose 
• 129173-16-6 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 176590-52-6 diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 

Relevant academic research and scientific papers

CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION

Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.

Syntheses of α- and β-C-glucopyranosyl serines from a common intermediate

(Chemical Equation Presented) A versatile synthesis leading to either C-linked α- or β-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the α-linkage. A transposition of these last steps leads to the α-linked isomer selectively.

IMMUNOGENS FOR MENINGITIDIS-A VACCINES

An oligosaccharide useful for a Meningitidis A vaccine contains a first mannose unit having a spacer in the alpha configuration at C-1, which spacer is capable of conjugating to a protein, and which is connected to a second mannose unit through a 1,6-linkage which connects C-6 of the first unit to C-1 of the second unit, wherein the 1,6-linkage comprises a phosphonate. Related methods of making such compounds, analogous compounds, or intermediates thereof are also disclosed.

Stereoselective synthesis of α-C-glucosyl serine and alanine via a cross-metathesis/cyclization strategy

(Chemical Equation Presented) C-Glycosyl amino acids represent stable mimics of monomeric units within natural O-linked glycoproteins. Olefin cross-metathesis has been used to provide alkene precursors for a mercury(II)-mediated cyclization, yielding α-C-

Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-α-D-glucosamine 1-phosphate and N-acetyl-α-D-mannosamine 1-phosphate

The isosteric phosphono analogues of N-acetyl-α-D-glucosamine 1-phosphate and N-acetyl-α-D-mannosamine 1-phosphate (1 and 2) are stereoselectively synthesized starting from 2,3,5-tri-O-benzyl-D-arabinose (3b). Reaction of 3b with divinylzinc stereoselectively affords the glucoenitol 4c, the mercuriocyclization and subsequent iododemercuriation of which stereoselectively afford the α-C-glucopyranosyl iodide 6b with a free hydroxyl group at C-2. Temporary protection of the hydroxyl group and treatment with triethyl phosphite converts 6b into the corresponding phosphonate 7b. The free hydroxyl group of 7b is then converted into an acetamido group by oximation, acetylation of the oxime, reduction, and subsequent acetylation. The reduction of the oxime with diborane stereoselectively affords the gluco isomer, whereas catalytic hydrogenation gives the manno isomer. Acetylation and deprotection afford the desired products 1 and 2.

Vinylation-Electrophilic Cyclization of Aldopentoses: Easy and Stereoselective Access to C-Glycopyranosides of Rare Sugars

A new C-glycosylation procedure, which involves vinylation of a properly protected aldopentose and mercuriocyclization of the obtained glycoenitol, is described; it allows C-glycopyranosides of rare sugars to be obtained from easily available pentoses. 2,

Stereochemistry of C-glycosidation through a Wittig-mercuriocyclization Procedure

The stereochemistry of C-glycosidation by reaction of the aldehydo group of the carbohydrate with methylenetriphenylphosphorane, and subsequent mercuriocyclization of the obtained product, has been investigated on different substrates.The procedure is ste