294872-82-5

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1115-97-5 trivinyl aluminum 

Downstream Products

• 485386-73-0 ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 
• 172223-08-4 diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 
• 172223-07-3 (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane 
• 176515-25-6 C₃₄H₄₂NO₉P 
• 908838-47-1 Methanesulfonic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 908838-46-0 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose 

Relevant academic research and scientific papers

Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.

[reaction: see text]This letter describes a single flask strategy to the synthesis of alpha-C-glycosides from glycals. This protocol couples a glycal epoxidation reaction with a C-2 alkoxy-directed carbon-carbon bond-forming reaction.

Highly stereoselective synthesis of C-vinyl pyranosides via a Pd 0-mediated cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enitols

Oct-2-enitols undergo a Pd0-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical pref

Synthesis of the C1-phosphonate analog of UDP-GlcNAc

We describe the first synthesis of the C1-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (Ki > 10 mM) of fungal chitin synthase

From α-1,2-Anhydrosugars to C-Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry

Ring opening of the epoxide function in α-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford α-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation α/β mixtures. Vinyl nucleophiles predominantly afford α-products, whereas allyl and allenyl species almost exclusively yield β-C-glycosides.

C-Glycosides to fused polycyclic ethers

This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions.