87316-20-9

Upstream product

• 67-56-1 methanol 
• 22860-24-8 5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl-dimethanesulfonate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 22860-25-9 methyl 2,3-dideoxy-4,6-dihydroxy-α-D-erythro-hex-2-enopyranoside 
• 137963-61-2 methyl 6-O-tert-butyldiphenylsilyl-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 

Downstream Products

• 137963-56-5 (2R,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide 
• 137963-57-6 (2S,4S,5R)-5-(tert-butyldiphenylsilyl)oxymethyl-4-methoxy-2-methyl-5-pentanolide 
• 137963-59-8 (4S,5R)-6-(tert-butyldiphenylsilyl)oxy-4-methoxy-2-hexen-5-olide 
• 137963-58-7 (4S,5R)-6-(tert-butyldiphenylsilyl)oxy-4-methoxy-5-hexanolide 
• 413193-26-7 (3aS,4R,6S,7aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-1-(4-methoxy-phenyl)-hexahydro-pyrano[4,3-d]oxazol-2-one 
• 413192-31-1 (4-methoxy-phenyl)-carbamic acid 2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester 
• 405145-64-4 methyl α-D-6-O-t-butyldiphenylsilyl-4-O-methanesulphonyl-2,3-dideoxyhex-2-enoerythropyranoside 
• 137963-60-1 methyl 6-O-tert-butyldiphenylsilyl-4-O-methyl-α-D-erythro-hex-2-enopyranoside 

Relevant academic research and scientific papers

Catalyst-Controlled Stereoselective O-Glycosylation: Pd(0) vs Pd(II)

Stereoselective construction of various O-glycosidic bonds was first achieved by different palladium sources using 3,4-O-carbonate galactal as the donor to reach yields up to 95% under mild conditions. With Pd(II) catalyst coordination of this glycal dono

Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-L-4-aminopent-2-enoglyceropyranosides

Starting from alkyl α-D-4-0-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatr

Unexpected stability of δ-lactones with axial substituents rather than equatorial ones. Conformational evaluation by molecular mechanics and molecular orbital calculations

A 1:1 mixture of the trisubstituted δ-lactones 5a and 5b was subjected to thermodynamically equilibrated conditions to give predominantly 5b with axial substituents rather than 5a with all equatorial ones, in contrast to the Prelog-Djerassi lactone derivatives 3a and 3b. Further surprisingly, it has been found that the disubstituted lactone 15 also adopts a half-chair conformation with axial substituents. The conformational analyses of these compounds by molecular mechanics and molecular orbital calculations have emphasized gauche effects and electrostatic interactions as a cause of the preference for axial conformers.

Unprecedented Stability of δ-Lactones with Axial Substituents rather than Equatorial ones; Comparison with the Prelog-Djerassi Lactone Derivative

A 1:1 mixture of the trisubstituted δ-lactones 11a and 11b was subjected to thermodynamically equilibrated conditions to give predominantly 11b with axial substituents rather than 11a with all equatorial ones, in contrast to the Prelog-Djerassi lactone derivatives 3a and 3b, and, further surprisingly, it has been found that the disubstituted lactone 10 also adopts a chair conformation with axial substituents.