200621-48-3

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 106-95-6 allyl bromide 
• 236424-93-4 methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside 
• 556-56-9 allyl iodid 
• 118545-10-1 (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran 
• 305815-34-3 [(2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol 
• 485386-44-5 ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 130523-98-7 (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 
• 90633-95-7 methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside 
• 236424-91-2 methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-(4-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside 
• 20231-38-3 (2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)tetrahydro-6-methoxy-2-((trityloxy)methyl)-2H-pyran-3-ol 
• 74024-29-6 methyl 4-O-allyl-2,3-di-O-benzyl-α-D-glucopyranoside 
• 87326-58-7 methyl 4-O-allyl-2,3-di-O-benzyl-6-O-trityl-α-D-glucopyranoside 

Downstream Products

• 200621-49-4 (1R,6R,8S,9R,10S)-9,10-bis(benzyloxy)-8-methoxy-2,7-dioxabicyclo[4.4.0]dec-4-ene 

Relevant academic research and scientific papers

Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when an unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined.

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.