126399-05-1

Basic information

• Product Name: (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol
• Synonyms: (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol
• CAS NO: 126399-05-1
• Molecular Weight: 234.338
• Mol File: 126399-05-1.mol

Chemical Properties

• CAS DataBase Reference: (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol(126399-05-1)
• EPA Substance Registry System: (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol(126399-05-1)

Safety Data

• Hazardous Substances Data: 126399-05-1(Hazardous Substances Data)

Upstream product

• 126399-04-0 (2E,4S,5S)-ethyl 5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate 
• 126399-03-9 cis/trans-(4S,5S)-ethyl-5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate 
• 126399-03-9 (E)-(S)-5-Methoxy-2,4-dimethyl-6-phenyl-hex-2-enoic acid ethyl ester 
• 176908-05-7 (2S,3S)-5-methoxy-2,3-dimethyl-6-phenylhex-2-ene 
• 122-78-1 phenylacetaldehyde 
• 184354-41-4 (2R,3S)-3-methoxy-2-methyl-4-phenylbutan-(N-methyl-O-methyl)-hydroxamide 
• 298202-04-7 (2'R,3'S,4R)-4-benzyl-3-[3'-hydroxy-2'-methyl-4'-phenylbutanol]-oxazolin-2-one 
• 134440-89-4 (2R,3S)-3-methoxy-2-methyl-4-phenylbutanal 
• 134440-87-2 (2'R,3'S,4R,5S)-3-(3'-hydroxy-2'-methyl-4'-phenylbutanoyl)-4-methyl-5-phenyloxazolidin-2-one 
• 184354-37-8 (2R,3S)-3-hydroxy-2-methyl-4-phenylbutan-(N-methyl-O-methyl)-hydroxamide 
• 100-58-3 phenylmagnesium bromide 
• 176908-04-6 ((E)-(2S,3S)-2-Methoxy-3-methyl-hex-4-enyl)-benzene 
• 176908-03-5 (E)-(2R,3S)-2-Methoxy-3-methyl-1-phenyl-hex-4-en-1-one 
• 177019-68-0 (E)-(2R,3S)-2-Methoxy-3-methyl-hex-4-enoic acid 

Downstream Products

• 126399-11-9 (2S,3S,4E)-6-bromo-2-methoxy-3,5-dimethyl-1-phenyl-4-hexene 
• 211816-22-7 2-<<(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl>sulfonyl>benzothiazole 
• 223689-25-6 2-<<(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl>thio>benzothiazole 
• 298202-05-8 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenal 
• 134440-92-9 (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid 
• 298202-08-1 (2E,4E,6S,7S)-7-methoxy-4,6-dimethyl-8-phenyl-2,4-octadienal 
• 298202-07-0 (2E,4E)-(6S,7S)-7-Methoxy-4,6-dimethyl-8-phenyl-octa-2,4-dien-1-ol 
• 298202-06-9 ethyl (2E,4E,6S,7S)-7-methoxy-4,6-dimethyl-8-phenyl-2,4-octadienoate 
• 298202-11-6 (3S,4S)-3-((1E,3E)-(5S,6S)-6-Methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-4-methyl-5-oxo-isoxazolidine-2-carboxylic acid tert-butyl ester 
• 298202-10-5 (2S,3R,4E,6E,8S,9S)-1-O-(tert-butoxycarbamoyl)-3-hydroxy-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoate 
• 298202-09-2 (2'S,3'R,4'E,6'E,8'S,9'S,4S)-4-benzyl-3-[3'-hydroxy-9'-methoxy-2',6',8'-trimethyl-10'-phenyl-4,6-decadienoyl]-oxazolin-2-one 
• 126399-06-2 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enyl(triphenyl)phosphonium bromide 
• 141672-08-4 (-)-motuporin 
• 194149-75-2 (E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadien-1-ol 

Relevant articles and documents

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A series of simplified microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for thei

Enantiospecific synthesis of N-Boc-Adda: a linear approach.

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Total synthesis of motuporin and 5-[L-Ala]-motuporin

Total synthesis of the cyclic peptide hepatotoxin motuporin is described, including an efficient synthesis of the constituent amino acid Adda. Three strategies to motuporin are outlined with their relative strengths and weaknesses. Cyclization of the linear peptide precursor was found to proceed moderately well for peptides containing the N- methyldehydrobutyrine residue masked as a threonine, but significant C- terminal epimerization occurred in the presence of the dehydroamino acid. Replacement of the N-methyldehydrobutyrine residue by L-alanine was explored to assess the contribution of this dehydroamino acid to the biochemical activity of motuporin. Some epimerization also was observed during cyclization of the alanine-containing peptide. Synthetic motuporin and both isomers of 5-[L-Ala]-motuporin inhibit the activity of protein phosphatase-1 (PP1) in rat adipocyte lysates with comparable IC50 values. These results indicate that the N-methyldehydrobutyrine residue is not essential for PP1 inhibition.

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N-Boc-Adda has been prepared in 15 steps and 9% overall yield from the readily available alcohol, 3-pentyne-2-ol, employing a route that includes two Claisen rearrangements.

Stereocontrolled Synthesis of (2S,3S,8S,9S,4E,6E)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic Acid (Adda), the Amino Acid Characteristic of Microcystins and Nodularin

(4R,5S)-4-Methyl-5-phenyloxazolidin-2-one has been used as a chiral template to construct the 8S and 9S chiral centres of (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the 2S and 3S centres being derived from D-asp