82659-57-2

Upstream product

• 762-72-1 allyl-trimethyl-silane 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 53008-62-1 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide 
• 2622-05-1 allylmagnesium bromide 
• 147242-49-7 (4-Nitro-phenyl)-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methanone 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 1730-25-2 allylmagnesium bromide 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 

Downstream Products

• 87256-54-0 (S)-1-((2R,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-ethane-1,2-diol 
• 87256-50-6 4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-yl)-but-2-en-1-ol 
• 87256-51-7 [(2R,3R)-3-((2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-methanol 
• 87263-31-8 (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butan-2-ol 
• 83861-86-3 (S)-1-{(4S,5R)-2,2-Dimethyl-5-[(R)-1-methyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-[1,3]dioxolan-4-yl}-pent-4-en-1-ol 
• 87256-52-8 (Z)-(6R,7R)-6-Hydroxy-7-methyl-8-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-oct-4-enoic acid 
• 87256-53-9 (S)-5-[(1S,2R,3R)-1,2-Dihydroxy-3-methyl-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl]-dihydro-furan-2-one 
• 77737-63-4 (2S,3S,4R,5S,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol 

Relevant academic research and scientific papers

Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group

C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.

Synthesis of β-C-galactosyl d- and l-alanines

Synthesis of β-C-d-galactosyl d- and l-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and SN2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.

Adaptable synthesis of C-glycosidic multivalent carbohydrates and succinamide-linked derivatization

A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic d-mannose, d-glucose, and d-galactose derivatives with different length C1-linked spacer un

Facile preparation of an orthogonally protected, pH-sensitive, bioconjugate linker for therapeutic applications

(Chemical Equation Presented) We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).