104372-54-5

Upstream product

• 104372-56-7 (2R,4E)-2-Methyl-4-hexen-1-ol 
• 84906-49-0 (2R,3R,5E)-3-methyl-5-heptene-1,2-diol 
• 1577-20-4 (E)-hex-4-enoic acid 
• 104324-24-5 (4R)-3-((4'E)-4'-hexenoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 104324-25-6 (4R)-3-((2'R,4'E)-2'-methyl-4'-hexenoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 118492-11-8 (4E)-2-Methyl-4-hexenoic acid 
• 118942-48-6 (E)-2-methylhex-4-enoic acid ethyl ester 
• 93553-73-2 (2R,4E)-2-Methyl-4-hexenoic acid 
• 118958-06-8 N-<(2R,4E)-2-Methyl-4-hexenoyl>-S-phenylglycinol 
• 82545-68-4 ethyl 2-methyl-2-carboethoxy-trans-4-hexenoate 
• 118430-63-0 (E)-2-Methyl-hex-4-enoyl chloride 
• 118430-65-2 (S)-N-<<(2S,4E)-2-methylhex-4-en>oyl> phenyl alaninol 
• 127949-94-4 2-((E)-(R)-2-Methyl-hex-4-enyloxy)-tetrahydro-pyran 
• 127949-88-6 2-((E)-But-2-enyl)-2-methyl-malonic acid 

Downstream Products

• 111610-37-8 (2R,5S,1'R,2'R)-5-((E)-1'-benzoyloxy-2'-methyl-4'-hexenyl)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 113122-47-7 (R)-4-Benzyl-3-((E)-(2R,3S,4R)-2-bromo-3-hydroxy-4-methyl-oct-6-enoyl)-oxazolidin-2-one 
• 135646-41-2 (4S,5R)-5-((E)-(R)-1-Methyl-pent-3-enyl)-2-oxo-oxazolidine-4-carboxylic acid benzyl ester 
• 135646-40-1 (2R,4S)-2-tert-Butyl-4-((E)-(1R,2R)-1-hydroxy-2-methyl-hex-4-enyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 135646-39-8 (2R,5S,6R)-1-aza-2-tert-butyl-3,7-dioxa-4,8-dioxo-6-<(1'R,3'E)-1'-methyl-3'-pentenyl>bicyclo<3.3.0>octane 
• 104324-19-8 (4S)-3-((4'S,5'R)-5'-((1R,3E)-1-methyl-3-pentenyl)-2'-thioxo-4'-oxazolidinylcarbonyl)-4-(phenylmethyl)-2-oxazolidinone 
• 113122-43-3 Methyl-carbamic acid (E)-(1S,2R)-1-[(R)-2-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-1-bromo-2-oxo-ethyl]-2-methyl-hex-4-enyl ester 
• 59865-23-5 (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid 
• 111610-38-9 (2R,5S,1'R,2'R)-5-((E)-1'-benzoyloxy-2'-methyl-4'-hexenyl)-2-(tert-butyl)-1,3-dimethylimidazolidin-4-one 
• 111646-96-9 (1R,2R,2'S,4E)-1-(N₁,N₂-dimethylglycinamide-2'-yl)-2-methyl-4-hexenyl benzoate 
• 81135-57-1 (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-amino-oct-6-enoic acid 

Relevant academic research and scientific papers

Synthesis and Structural Confirmation of (2S,3R,4R,6E)-2-Acetylamino-3-hydroxy-4-methyl-6-octenoic Acid, a New Amino Acid Produced by Neocosmospora vasinfecta

An unusual amino acid, (2S,3R,4R,6E)-2-acetylamino-3-hydroxy-4-methyl-6-octenoic acid (2a) and its stereoisomer (2b), were synthesized by the aldol condensation of (2R,4E)-2-methyl-4-hexenal (5) with tert-butyl isocyanoacetate (6) as the key reaction via trans-oxazoline derivative 7, in which two continuous chiral centers were newly formed.The oxazoline derivative was efficiently hydrolyzed to afford separable N-formyl-β-hydroxy amino acid esters 8a and 8b in a 1:1 ratio.Each diastereomer was transformed into target N-acetyl amino acids 2a and 2b via corresponding amino acids 1a and 1b.

A VERSATILE PROTOCOL FOR β-HYDROXY-α-AMINO ACIDS: AN APPLICATION TO (4R)-4--4,N-DIMETHYL-L-THREONINE (MeBmt)

cis-Oxazolidinone derivative (30) readily realised from chiral 2,3-epoxy alcohol (27) had been exploited in the synthesis of (4R)-4--4,N-dimethyl-L-threonine (2), an unusual β-hydroxy-α-amino acid present in cyclosporin.The intrinsic featur

A STEREOSPECIFIC SYNTHESIS OF (4R)-4--4,N-DIMETHYL-L-THREONINE (MeBmt)

The utility of readily obtainable cis-oxazolidinone derivative (14) has been explored for the efficient and stereospecific synthesis of (4R)-4--4,N-dimethyl-L-threonine, an unusual syn-β-hydroxy-α-amino acid of cyclosporine.

Preparative-Scale, Facile Synthesis of (2R,4E)-2-Methyl-4-hexenal: A Key Intermediate of (2S,3R,4R,6E)-3-Hydroxy-4-methyl-2-methylamino-6-octenoic Acid (MeBmt)

Facile separation and mild acidic hydrolysis of the diastereomeric amides derived from 2-methyl-4-hexenoic acid and L-2-phenylglycinol are used in a rapid, preparative-scale synthesis of (2R,4E)-2-methyl-4-hexenal, a key intermediate of MeBmt.

Asymmetric Glycine Enolate Aldol Reactions: Synthesis of Cyclosporine's Unusual Amino Acid, MeBmt

The chiral glycine synthon, 3c, as its derived stannous enolate, has been demonstrated to undergo a highly syn diastereoselective aldol addition reaction with representative aldehydes to give the adducts 5 (R = C6H5, Me, Me2CH) in yields ranging from 71 to 92percent.The utility of these intermediates has been demonstrated via the subsequent three-step transformation of these adducts to the enantiomerically pure N-methyl β-hydroxy amino acids 1.This reaction methodology has been applied to the asymmetric synthesis of (4R)-4-((E)-2-butenyl)-4,N-dimethyl-L-threonine (1a), an important constituent in the immunosuppressant peptide cyclosporine.Several additional structural analogues of 1a were also prepared in conjunction with this study.