188729-96-6

Basic information

• Product Name: Hexanal, 2-methyl-6-(phenylmethoxy)-, (2S)-
• CAS NO: 188729-96-6
• Molecular Formula: C14H20O2
• Molecular Weight: 220.312
• Mol File: 188729-96-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Hexanal, 2-methyl-6-(phenylmethoxy)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexanal, 2-methyl-6-(phenylmethoxy)-, (2S)-(188729-96-6)
• EPA Substance Registry System: Hexanal, 2-methyl-6-(phenylmethoxy)-, (2S)-(188729-96-6)

Safety Data

• Hazardous Substances Data: 188729-96-6(Hazardous Substances Data)

Upstream product

• 143761-23-3 (+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone 
• 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 
• 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 
• 193146-31-5 [(S)-6-Benzyloxy-2-methyl-hex-(E)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 188729-97-7 (S)-6-benzyloxy-2-methyl-1-hexanol 

Downstream Products

• 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 
• 188729-99-9 [(S)-6-benzyloxy-2-methyl-hexyloxy]-tert-butyl-dimethyl-silane 
• 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 articles and documents

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.