179944-92-4

Upstream product

• 24074-26-8 ethyl (diisopropylphosphoryl)acetate 
• 179944-91-3 (2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 207572-38-1 (E)-(4R,5S,6R)-7-Benzyloxy-5-hydroxy-4,6-dimethyl-hept-2-enoic acid ethyl ester 
• 119065-12-2 (3R,4S,5R)-6-(benzyloxy)-3,5-dimethyl-1-hexen-4-ol 
• 179944-89-9 (4S,5R)-3-((2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 157430-96-1 (2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide 
• 179944-90-2 (2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanoic acid methoxy-methyl-amide 
• 207572-37-0 (E)-3-[(2S,3R)-3-((R)-2-Benzyloxy-1-methyl-ethyl)-oxiranyl]-acrylic acid ethyl ester 
• 125873-80-5 ((2S,3R)-3-((R)-1-(benzyloxy)propan-2-yl)oxiran-2-yl)methanol 
• 443283-58-7 [(1S,2R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-but-3-enyloxy]-tert-butyl-dimethyl-silane 
• 79026-61-2 (R)-3-benzyloxy-2-methylpropanal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 157430-97-2 (E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol 
• 207572-43-8 (4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptanoic acid ethyl ester 
• 862096-08-0 (4S,7R,8S,9R)-10-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,7,9-trimethyl-dec-1-en-4-ol 
• 862096-09-1 (4S,7R,8S,9R)-10-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7,9-dimethyl-decan-2-one 
• 862096-22-8 [(1S,2R,5S)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-5-(4-methoxy-benzyloxy)-2,7-dimethyl-oct-7-enyloxy]-tert-butyl-dimethyl-silane 
• 862096-15-9 (3R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-10,12-dimethyl-tridec-1-en-5-one 
• 862096-13-7 (3R,7S,10R,11S,12R)-13-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-7-(4-methoxy-benzyloxy)-10,12-dimethyl-tridec-1-en-5-one 
• 862096-26-2 (3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol 
• 862096-24-0 (3R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-10,12-dimethyl-tridec-1-en-5-one 
• 207572-44-9 (4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptanal 
• 144604-71-7 (βR,2S,3R,6S,8S)-2-[α-(tert-butyldiphenylsilyloxy)ethyl]-β,3-dimethyl-1,7-dioxaspiro[5.5]undecane-8-ethanol 
• 207572-39-2 (9R,10S,11R)-12-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-9,11-dimethyl-dodec-1-en-6-ol 
• 207572-36-9 [(2S,6S,8S,9R)-8-((R)-2-Benzyloxy-1-methyl-ethyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid methyl ester 
• 207572-40-5 (9R,10S,11R)-12-Benzyloxy-10-(tert-butyl-dimethyl-silanyloxy)-9,11-dimethyl-dodec-1-en-6-one 

Relevant academic research and scientific papers

Stereoselective synthesis of the C1-C13 segment of dolabelide B

The efficient construction of the C1-C13 segment of dolabelide B is described. A key element of the synthesis entails BITIP catalyzed asymmetric methallylation to establish the C7 stereocenter, which was then used to direc

Stereoselective synthesis of spiroketal moiety of ionophore antibiotic routiennocin

A synthetic route to optically pure spiroketal moiety comprising C8- C20 segment of ionophore antibiotic routiennocin is described.

Aplyronine A, a potent antitumor substance of marine origin, aplyronines B and C, and artificial analogues: Total synthesis and structure-cytotoxicity relationships

The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent approach. Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by Julia olefination with sulfone 8 gave the C5-C20 segment 9, while the Julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) and C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.