134440-92-9

Basic information

• Product Name: (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid
• Synonyms: (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid
• CAS NO: 134440-92-9
• Molecular Weight: 431.572
• Mol File: 134440-92-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid(134440-92-9)
• EPA Substance Registry System: (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid(134440-92-9)

Safety Data

• Hazardous Substances Data: 134440-92-9(Hazardous Substances Data)

Upstream product

• 126399-11-9 (2S,3S,4E)-6-bromo-2-methoxy-3,5-dimethyl-1-phenyl-4-hexene 
• 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 
• 298202-04-7 (2'R,3'S,4R)-4-benzyl-3-[3'-hydroxy-2'-methyl-4'-phenylbutanol]-oxazolin-2-one 
• 298202-06-9 ethyl (2E,4E,6S,7S)-7-methoxy-4,6-dimethyl-8-phenyl-2,4-octadienoate 
• 298202-07-0 (2E,4E)-(6S,7S)-7-Methoxy-4,6-dimethyl-8-phenyl-octa-2,4-dien-1-ol 
• 298202-08-1 (2E,4E,6S,7S)-7-methoxy-4,6-dimethyl-8-phenyl-2,4-octadienal 
• 298202-05-8 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenal 
• 184354-41-4 (2R,3S)-3-methoxy-2-methyl-4-phenylbutan-(N-methyl-O-methyl)-hydroxamide 
• 122-78-1 phenylacetaldehyde 
• 126399-04-0 (2E,4S,5S)-ethyl 5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate 
• 126399-05-1 (2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-en-1-ol 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 194149-71-8 (E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene 
• 194149-68-3 (R)-Azido-[(2R,3S,4R)-3-(dimethyl-phenyl-silanyl)-4-methyl-tetrahydro-furan-2-yl]-acetic acid methyl ester 

Downstream Products

• 225781-02-2 Boc-Adda-D-iso-Glu(OMe)-N-(Me)-Gly-D-Ala-L-Leu-D-β-Me-iso-Asp(OMe)-L-Ala-OH 
• 225781-01-1 Boc-Adda-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-D-β-Me-iso-Asp(OMe)-L-Ala-OH 
• 225780-68-7 Boc-Adda-D-iso-Glu(OMe)-MeΔAla-D-Ala-3-cyclohexyl-L-Ala-D-β-Me-iso-Asp(OMe)-L-Ala-OH 
• 225781-00-0 Boc-Adda-D-iso-Glu(OMe)-MeΔAla-N²-Boc-N³-Troc-(R)-aminoala-L-Leu-D-β-Me-iso-Asp(OMe)-L-Ala-OH 
• 223923-83-9 Dimethylmotuporin 
• 223923-68-0 (2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid 
• 223923-94-2 (2S,5R,6S,9R,12S,13S,16R)-9-Isopropyl-12-((1E,3E)-(5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-1,2,6,13-tetramethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaaza-cyclononadecane-5,16-dicarboxylic acid dimethyl ester 
• 223923-93-1 (2S,5R,6S,9S,12S,13S,16R)-9-Isopropyl-12-((1E,3E)-(5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-1,2,6,13-tetramethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaaza-cyclononadecane-5,16-dicarboxylic acid dimethyl ester 
• 223923-92-0 3-(1-allyloxycarbonyl-2-methyl-propylcarbamoyl)-2-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-propionylamino)-butyric acid methyl ester 
• 223924-04-7 2-[3-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-3-methoxycarbonyl-2-methyl-propionylamino]-3-methyl-butyric acid 
• 223923-79-3 3-(1-allyloxycarbonyl-2-methyl-propylcarbamoyl)-2-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-but-2-enoylamino)-butyric acid methyl ester 
• 223924-03-6 3-(1-allyloxycarbonyl-2-methyl-propylcarbamoyl)-2-(2-{[4-(3-tert-butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyrylamino)-butyric acid methyl ester 

Relevant articles and documents

Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays

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

Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin

A highly convergent asymmetric synthesis of the protein phosphatase inhibitor motuporin 1a is described. Synthesis and coupling of the individual peptide fragments [34 + -35 → 51] followed by macrocyclization afforded the fully protected motuporin precursor 33, which is converted to the natural product by dehydration and ester hydrolysis, Six of the eight stereogenic centers associated with the natural product were introduced using asymmetric crotylsilane bond construction methodology. Our approach features an efficient Pd(0)-catalyzed cross-coupling reaction between a configurationally well-defined vinyl zinc intermediate 22 and an (E)-vinyl iodide 7, which afforded compound 43, resulting in the construction of the trisubstituted (E,E)-diene system of the motuporin side chain. Improved reaction conditions for macrocyclization in the formation of 33 are also detailed.

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

[structure: see text] Synthesis of the unusual amino acid (2S,3S,8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 1

Total synthesis of motuporin (nodularin-v)

The serine/threonine phosphatase (protein phosphatase 1 and 2A) inhibitors constitute a biologically and structurally interesting class of natural products. Among this class of inhibitors are cyclic pentapeptides (nodularins) and cyclic heptapeptides (mic

An asymmetric synthesis of ADDA, and ADDA-glycine dipeptide using the ss-lactam synthon method

The paper describes the synthesis of the W-Boc lactam 4, and demonstrates that it is an important intermediate in the synthesis of dipeptide 5 (X = H, n = 0, R = Me), an analogue of the ADDA-GIu dipeptide 3. In addition we have described a mild method for the preparation of the amino acid salt ADDA-HC1, and provided synthetic methods, and full characterisation for the previously 'elusive' free amino acid ADDA.

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.

Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting from (S)-serine and (S)-phenyllactic acid

The important naturally occurring β-amino acid N-Boc-ADDA is prepared following a disconnection of the C-C bond between the two E,E double bonds. The stereochemistry of the two synthons was controlled using the alkylation of chiral bromoallenes derived fr

A new stereoselective route to (2S, 3S, 8S, 9S, 4E, 6E)-3-amino-9-methoxy-2, 6, 8-trimethyl-10-phenyldeca-4, 6-dienoic acid (Adda)

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.