96203-95-1

Basic information

• Product Name: Oxirane, 2-[2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl]-2-methyl-, (S)-
• CAS NO: 96203-95-1
• Molecular Formula: C16H24O3
• Molecular Weight: 264.365
• Mol File: 96203-95-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Oxirane, 2-[2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl]-2-methyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, 2-[2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl]-2-methyl-, (S)-(96203-95-1)
• EPA Substance Registry System: Oxirane, 2-[2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl]-2-methyl-, (S)-(96203-95-1)

Safety Data

• Hazardous Substances Data: 96203-95-1(Hazardous Substances Data)

Upstream product

• 85148-25-0 (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol 
• 98-59-9 p-toluenesulfonyl chloride 
• 130627-49-5 (2S,5S)-2-(tert.-Butyl)5-<2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl>-1,3-dioxolan-4-on 
• 103808-37-3 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester 
• 103808-39-5 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1R,2S,3S,4S)-3-benzyl-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>ester 
• 130627-47-3 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1S)-1-(benzylcarbamoyl)-ethyl>ester 
• 103808-44-2 4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-oxobutansaeure-<(1S)-1-(benzylcarbamoyl)-ethyl>ester 
• 130627-48-4 (S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxybutansaeure 
• 103808-41-9 4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-oxobutansaeure 
• 130627-46-2 4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-oxobut-3-ensaeure 
• 103808-42-0 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde 
• 13199-54-7 1,4-dimethoxy-2,3,5,6-tetramethylbenzene 
• 527-17-3 Duroquinone 
• 527-18-4 Durohydroquinone 

Downstream Products

• 7559-04-8 2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione 
• 59-02-9 Tocopherol 
• 91418-95-0 (3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethyl-hexadecan-3-ol 

Relevant articles and documents

Total synthesis of naturally occurring α-tocopherol. Assymetric alkylation and asymmetric epoxidation as means to introduce (R)-configuration at C(2) of the chroman moiety

Based on the reductive, stereospecific ring closure of (2R,4'R,8'R)-α-'Tocopherylquinone' or corresponding analogues with a short, functionalized side chain (B, Scheme 1) to 1 resp. the chroman system of 1 (C), two different approaches for the introduction of the required tertiary methyl-substituted alcohol structure in the side chain of the aromatic precursors (A, Scheme 1) were developed. The first approach uses asymmetric alkylation in three different versions featuring a) diastereoselective steering with chiral auxiliaries I-IV (Scheme 2) attached as esters to α-keto acids, b) intermediate transfer of chirality in an ester enolate (from 18, Scheme 4) derived from an optically active α-hydroxyacid, c) enantioselective alkylation of phytenal (20) and subsequent ring closure with chirality transfer (Schemes 5-7). The second approach is based on the asymmetric epoxidation of β-metallylalcohol (Sharpless epoxidation), the corresponding epoxyalcohol being converted in situ to the (S)- or (R)-chlorodiol (S)- and (R)-29, respectively, for isolation (Schemes 8 and 9). Nucleophilic epoxide opening with a (3R,7R)-3,7,11-trimethyldodecyl (C15**) and an ArCH2 unit in appropriate sequence is used to assemble the C-framework of the target molecule via corresponding epoxide intermediates from either chlorodiol. Combined with the use of the methoxymethyl-ether function for protection of the hydroquinone system, the epoxide approach provides a short route to 1 (Scheme 10).

Hydroquinone derivatives and a process for their preparation

Compound of the general formula STR1 wherein R represents an ether protecting group useful as intermediates.