188729-96-6

Upstream product

• 193146-31-5 [(S)-6-Benzyloxy-2-methyl-hex-(E)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 190712-20-0 ((S)-6-Benzyloxy-2-methyl-hexyloxy)-tert-butyl-diphenyl-silane 
• 190712-18-6 (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hex-3-en-1-ol 
• 143761-23-3 (+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone 
• 188729-97-7 (S)-6-benzyloxy-2-methyl-1-hexanol 
• 190712-19-7 (S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexan-1-ol 
• 671207-31-1 (S)-4-benzyl-3-[(S)-6-benzyloxy-2-methyl-hexanoyl]-oxazolidin-2-one 

Downstream Products

• 188729-99-9 [(S)-6-benzyloxy-2-methyl-hexyloxy]-tert-butyl-dimethyl-silane 
• 190712-23-3 (4R,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 190712-22-2 (2R,3S,4S)-8-Benzyloxy-2,3-dihydroxy-4-methyl-octanoic acid methyl ester 
• 190712-24-4 [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 
• 186692-73-9 desoxyepothilone A 
• 201683-59-2 (3S,6R,7S,8S)-12-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,6,8-tetramethyl-5-oxo-dodecanoic acid tert-butyl ester 
• 201683-57-0 (4R,5S,6S)-10-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-decan-3-one 
• 201683-56-9 1-[(2R,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-one 
• 1026479-66-2 (4R,5S,6S)-10-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2,2,4,6-tetramethyl-decan-3-one 
• 201683-58-1 (4R,5S,6S)-10-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,4,6-tetramethyl-decan-3-one 
• 201683-53-6 1-[(2S,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-ol 
• 201683-52-5 3-[(2S,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-hydroxy-2,2-dimethyl-propionic acid methyl ester 
• 201683-50-3 (E)-(S)-8-Benzyloxy-2,4-dimethyl-oct-2-en-1-ol 
• 201683-51-4 [(2S,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-methanol 

Relevant academic research and scientific papers

Radical-induced opening of trisubstituted epoxides: Application in the synthesis of C1-C12 segment of epothilones

Diastereo- and regioselective opening of a trisubstituted epoxy ketone at the more substituted carbon using samarium(II) iodide presents an alternate approach to the C5-C7 aldol moiety with β-hydroxyketo framework in the stereoselective synthesis of C1-C12 segment of epothilones.

Total syntheses of epothilones A and B via a macrolactonization-based strategy

The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization ofintermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.

Synthetic studies of microsclerodermins. A stereoselective synthesis of a core building block for (2S,3R,4S,5S,6S,11E)-3-Amino-6-methyl-12- (4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD)

A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12- (4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (2, AMMTD) has been efficiently synthesized using the Sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a ni

Total synthesis of epothilone A: The macrolactonization approach

This highly convergent and practical total synthesis of the antitumor agent epothilone A uses a macrolactonization as the key step. The strategy may provide access to a variety of epothilones desirable for biological screening.