200621-39-2

Upstream product

• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 135560-96-2 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((E)-styryl)-tetrahydro-pyran-3-ol 
• 135637-05-7 2-(3',4',6'-tri-O-benzyl-α-D-glucopyranosyl)-(Z)-styrene 
• 200621-43-8 (3,4,6-tri-O-benzyl-β-D-glucopyranosyl)(phenyl)ethyne 
• 200621-47-2 (4S,5R,6S,7S,8R)-1,2-anhydro-6,7,9-tribenzyloxypyrano<4,5>pyran 
• 200621-41-6 cis-1-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylethene 
• 200621-44-9 cis-1-(2-O-allyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-phenylethene 
• 914657-29-7 2-(3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)-(Z)-styrene 
• 200621-42-7 (1R,6R,8R,9R,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0]dec-4-ene 
• 200621-45-0 (1R,6S,8R,9R,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0]dec-4-ene 

Relevant academic research and scientific papers

Zinc-mediated synthesis of α-C-glycosides from 1,2-anhydroglycosides

α-C-Glycosides have been prepared by the addition of organozinc reagents to glycal epoxides. Dialkyl and diaryl zinc reagents in the presence of CF3COOH provide the corresponding α-glycosides in 53-82% yields. Organozinc chlorides RZnC1 formed

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.

A convenient route to cis- and trans-fused bicyclic ethers by ruthenium mediated ring-closing metathesis of diene and enyne carbohydrate derivatives

A general approach towards the construction of highly functionalised pyranopyran and pyranofuran systems via Grubbs [Ru] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-propargyl functions on monosaccharide scaffolds is describ

A Novel Approach Towards cis- and trans-Fused Pyranopyrans Based on Ring-Closing Metathesis Reaction of Carbohydrate Derivatives

A novel synthesis of both cis- and trans-fused pyranopyran systems, based on ring-closing metathesis of glycal derived dienes, is described. Isomerisation of the resulting allylic double bond provides a new cyclic enol ether, thus opening the way to an iterative synthesis of cis-(trans-)fused cyclic polyethers.