65827-63-6

Upstream product

• 79218-91-0 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyramose 
• 100-39-0 benzyl bromide 
• 65827-57-8 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 67-56-1 methanol 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 64-19-7 acetic acid 
• 67965-11-1 (3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-2-ethoxy-2-methyl-5-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran 
• 60887-27-6 2-O-allyl-3,4-di-O-benzyl-D-glucopyranose 

Downstream Products

• 1010440-32-0 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α- and β-D-glucopyranose 
• 65827-57-8 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose 
• 79218-89-6 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 79218-88-5 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-β-D-mannopyranoside 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 79218-90-9 6-O-acetyl-3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 

Relevant academic research and scientific papers

Regio- and Stereoselective Synthesis of 1,2- cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis

Regio- and stereoselective synthesis of 1,2-cis-glycosides has been achieved by catalytic anomeric O-alkylation using organoboron compounds. Modulating steric and electronic factors of both catalysts and substrates enables activation of the axially oriented anomeric oxygens of glucose-derived dialkoxyborates. The mild reaction conditions allow broad functional-group tolerance. This approach can be applied to the efficient sequential synthesis of oligosaccharides.

Carbohydrate-based VEGF inhibitors

Cyclic peptide-carbohydrates (compounds 1a-c, 2, 33, 34) were designed and synthesized to act as mimetics of loop 2 of the proangiogenic molecule vascular endothelial growth factor D (VEGF-D). The mimetics were designed to inhibit dimerization of the receptors (VEGFR-2 and VEGFR-3) by VEGF-D, and thus have the potential to inhibit angiogenesis. To this end, in the previously described cyclic octapeptide CNEESLIC and the cyclic nonapeptide CGNEESLIC inhibitors derived from VEGF-D loop 2, the NEES tetrapeptide residue was replaced by a carbohydrate scaffold having the amino acid side chain mimics in positions proposed by modeling studies. Attachment of the additional amino acids using the Fmoc technology, then formation of the cyclic disulfides, and finally total deprotection afforded the target molecules of which 2 and 34 showed an ability to inhibit the biological activity of VEGF-D through VEGFR-2 in cell-based assays, albeit at high mimetic concentration. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

SYNTHESIS OF A MODEL OF AN IMMER CHAIN OF CELL-WALL PROTEOHETEROGLYCAN ISOLATED FROM Piricularia oryzae: BRANCHED D-MANNOPENTAOSIDES

Efficient syntheses are described of the branched D-mannopentaosides methyl 2,6-di-O-(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside and methyl 2,4-di-O-(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside, starting from the gly

Synthesis of benzyl and allyl ethers of D-glucopyranose

Starting from allyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside as a key intermediate, the following crystalline compounds were prepared: 2-O-allyl-3,4,6-tri-O-benzyl-D-glucopyranose (11) and its p-nitrobenzoate; 2,3,5-tri-O-benzyl-D-arabinofuranose (12) and the corresponding arabinitol; allyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (7); 3,4,6-tri-O-benzyl-D-glucopyranose (8); 2-O-allyl-3,4-di-O-benzyl-D-glucopyranose (17) and its bis(p-nitrobenzoate); and 3,4-di-O-benzyl-D-glucopyranose (19). The p-nitrobenzoates of compounds 11 and 17 are potential intermediates for the synthesis of the glycolipids of the cytoplasmic membranes of Streptococci.