137963-61-2

Upstream product

• 22860-24-8 5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl-dimethanesulfonate 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 151519-02-7 pironetin 
• 172603-10-0 Methyl 2,3-di-O-benzyl-6-dehydro-4-deoxy-4-C-ethyl-α-D-gulopyranoside 
• 172603-09-7 Methyl 2,3-di-O-benzyl-4-deoxy-4-C-ethyl-α-D-gulopyranoside 
• 172603-07-5 Methyl 6-O-(tert-butyldiphenylsilyl)-4-deoxy-4-C-ethyl-α-D-gulopyranoside 
• 172603-19-9 (2S,3R,4R,5R,6R,2'S,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanol 
• 172603-20-2 (2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal 
• 172603-22-4 (2S,3R,4R,5R,6R,5'S,6'R,7'R,8'R)-(2'E)-9'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-6'-methoxy-8'-<(methoxymethyl)oxy>-5',7'-dimethyl-2'-nonene 
• 172603-08-6 Methyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-4-C-ethyl-α-D-gulopyranoside 
• 172603-21-3 (2S,3R,4R,5R,6R,5'S,6'R,7'R,8'R)-(3'E)-9'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-6'-methoxy-8'-<(methoxymethyl)oxy>-5',7'-dimethyl-3'-nonen-2'-one 
• 172603-17-7 (2S,3R,4R,5R,6R,2'R,3'S,4'R,5'R)-1'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-6'-<(tert-butyldiphenylsilyl)oxy>-4'-methoxy-3',5'-dimethyl-2'-hexanol 
• 172603-16-6 (2S,3R,4R,5R,6R,3'S,4'R,5'R)-(1'Z)-1'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-6'-<(tert-butyldiphenylsilyl)oxy>-4'-methoxy-3',5'-dimethyl-1'-hexene 
• 172603-18-8 (2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-1'-<(tert-butyldiphenylsilyl)oxy>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethylhexane 
• 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 

Relevant academic research and scientific papers

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.

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.