494212-11-2

Upstream product

• 494212-08-7 methyl 2-deoxy-6-O-(triisopropylsilyl)-α-D-lyxo-hexopyranoside 
• 3971-45-7 methyl 2-deoxy-α-D-galactopyranoside 
• 4098-06-0 triacetyl-D-galactal 
• 124751-19-5 (2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 
• 494212-09-8 methyl 3,4-di-O-benzyl-2-deoxy-6-O-(triisopropylsilyl)-α-D-lyxo-hexopyranoside 
• 21193-75-9 D-galactal 
• 136656-50-3 (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane 
• 100-39-0 benzyl bromide 

Downstream Products

• 1056474-84-0 methyl 3,4-di-O-benzyl-2-deoxy-6-O-carbamoyl-α-D-lyxo-hexopyranoside 
• 1056474-83-9 methyl 3,4-di-O-benzyl-2-deoxy-6-O-(N-ethylcarbamoyl)-α-D-lyxo-hexopyranoside 
• 494212-13-4 methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-L-erythro-pentopyranoside 
• 494212-14-5 (2R,3R,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-2-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-pyran 
• 494212-12-3 methyl 3,4-di-O-benzyl-2,6,7-trideoxy-α-D-lyxo-hept-6-enopyranoside 

Relevant academic research and scientific papers

Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides

The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (α or β, respectively).

Direct carbohydrate to carbocycle conversions via intramolecular allylation with Et2Zn/Pd(0)

Treatment of 5-vinylpyranosides with Et2Zn and catalytic Pd(0), in the presence of ZnCl2, results in the formation of 5-membered carbocyclic products. This carbohydrate ring-contraction features an intramolecular allylation of a ring-opened carbohydrate aldehyde by an in situ-generated nucleophilic allylzinc species. The stereoselectivity about vinyl and free hydroxyl groups at the newly created stereogenic centers varies from low to moderate while both its extent and sense are found to depend on particular structural features (e.g. the configuration of the starting carbohydrate).

Acetal-vinyl sulfide cyclization on sugar substrates: Effect of structure and substituent

A range of 2-deoxyfuranoside and -pyranoside derivatives were fashioned into derivatives that carry a vinyl or propenyl side chain. Extension of the alkene by a Suzuki cross-coupling reaction with 1-bromo-1-(phenylthio)ethene gave thioenol ethers as the cyclization substrates. The treatment of these substrates with BF3·Et2O in tert-butylmethyl ether below 0 °C induced cyclization to optically active bicyclic ethers. If the cyclizations are carried out in toluene as the solvent, the isomerization of the terminal thioenol ether to the inner thioenol ether can take place prior to the cyclization. The cyclization reactions can be impeded by steric and electronic factors. The opening of the bicyclic ethers could be illustrated with the base-induced conversion of the ketone 53 to the cyclooctenone 54.