179944-96-8

Basic information

• Product Name: 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-7-phenylsulfanyl-heptyl ester
• Synonyms: 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-7-phenylsulfanyl-heptyl ester
• CAS NO: 179944-96-8
• Molecular Weight: 482.8
• Mol File: 179944-96-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-7-phenylsulfanyl-heptyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-7-phenylsulfanyl-heptyl ester(179944-96-8)
• EPA Substance Registry System: 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-7-phenylsulfanyl-heptyl ester(179944-96-8)

Safety Data

• Hazardous Substances Data: 179944-96-8(Hazardous Substances Data)

Upstream product

• 179944-89-9 (4S,5R)-3-((2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 179944-94-6 2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester 
• 179944-92-4 (E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl ester 
• 157430-96-1 (2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide 
• 179944-93-5 {(2S,3S)-3-[(1R,2R,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-oxiranyl}-methanol 
• 157430-97-2 (E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol 
• 157430-98-3 (3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol 
• 179944-91-3 (2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal 
• 179944-90-2 (2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanoic acid methoxy-methyl-amide 
• 3282-30-2 pivaloyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 882-33-7 diphenyldisulfane 
• 179944-95-7 2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-3,7-dihydroxy-4,6-dimethyl-heptyl ester 

Downstream Products

• 179944-97-9 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-7-phenylsulfanyl-3-triethylsilanyloxy-heptyl ester 
• 157430-99-4 2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-10-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-4,6-dimethyl-3-triethylsilanyloxy-decyl ester 
• 157430-91-6 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester 
• 179945-07-4 2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9,15-dimethoxy-4,6,10,13-tetramethyl-16-trityloxy-hexadec-10-enyl ester 
• 179945-08-5 2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester 
• 157542-64-8 2,2-Dimethyl-propionic acid (Z)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-triethylsilanyloxy-16-trityloxy-hexadec-10-enyl ester 
• 157431-01-1 2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-triethylsilanyloxy-16-trityloxy-hexadec-10-enyl ester 

Relevant articles and documents

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.