179944-88-8

Upstream product

• 179945-23-4 [(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butoxy]-tert-butyl-diphenyl-silane 
• 179945-15-4 (4R,5S,E)-ethyl 6-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methylhex-2-enoate 
• 179945-18-7 Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester 
• 179945-17-6 {(2S,3S)-3-[(1R,2S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-oxiranyl}-methanol 
• 162255-09-6 <2S,3S>-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-4-(phenylmethoxy)butanal 
• 157318-10-0 (4S,5R)-3-((2S,3S)-4-Benzyloxy-3-hydroxy-2-methyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 179945-22-3 (2S,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-2-ol 
• 157220-45-6 <2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide 
• 179945-19-8 (3R,4R,5R,6S)-7-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3,5-dimethyl-heptanenitrile 
• 157220-46-7 (2R,3R,4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hexane-1,3-diol 
• 179945-16-5 (E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol 
• 162255-08-5 (2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide 
• 179945-21-2 (2S,3S)-3-((2R,3R)-5-Methoxy-3-methyl-tetrahydro-furan-2-yl)-butane-1,2-diol 
• 909803-79-8 (4R,5R,6R)-4-((R)-3,3-Dimethoxy-1-methyl-propyl)-2,2,5-trimethyl-6-((E)-propenyl)-[1,3]dioxane 

Downstream Products

• 188359-30-0 (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan 
• 909803-74-3 (3R,4R,5R,6R,9S,10S,12S,13R)-12,14-Bis-(tert-butyl-diphenyl-silanyloxy)-6-(3,4-dimethoxy-benzyloxymethoxy)-10-methoxy-3,5,9,13-tetramethyl-1-trityloxy-tetradecan-4-ol 
• 740836-13-9 (3R,4R,5R,6R,9S,10S,12S,13R)-12,14-Bis-(tert-butyl-diphenyl-silanyloxy)-6-(3,4-dimethoxy-benzyloxymethoxy)-10-methoxy-3,5,9,13-tetramethyl-tetradecane-1,4-diol 
• 740836-12-8 (2R,3R)-2-[(1S,2R,5S,6S,8S,9R)-8,10-Bis-(tert-butyl-diphenyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethoxy)-6-methoxy-1,5,9-trimethyl-decyl]-5-methoxy-3-methyl-tetrahydro-furan 
• 740836-26-4 (2R,3R)-2-[(1S,2R,5S,6S,8S,9R)-8,10-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethoxy)-6-methoxy-1,5,9-trimethyl-decyl]-5-methoxy-3-methyl-tetrahydro-furan 
• 740836-11-7 (2R,3R)-2-[(E)-(1S,2R,5S,6S,8S,9R)-2-Benzyloxy-8,10-bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,5,9-trimethyl-dec-3-enyl]-5-methoxy-3-methyl-tetrahydro-furan 
• 740836-27-5 (2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol 

Relevant academic research and scientific papers

Synthesis and biological activity of mycalolide analogs

Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The an

Synthesis and actin-depolymerizing activity of mycalolide analogs

Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), was stereoselectively synthesized and was found to have strong actin-depolymerizing activity.

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.

Synthetic studies on aplyronine A, a potent antitumor substance of marine origin: Stereocontrolled synthesis of the C21-C34 segment

The C21-C34 segment 2 of aplyronine A (1), a potent antitumor substance of marine origin, was synthesized enantioselectivity in 25 steps (17% overall yield) from imide 11.