108794-12-3

Upstream product

• 65253-04-5 (-)-8-phenylmenthol 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 215321-43-0 Chloro-oxo-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 

Downstream Products

• 118466-98-1 O-[(2S)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol 
• 128114-53-4 8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate 
• 128162-89-0 8-Phenylmenthyl (2R,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate 
• 128162-88-9 8-Phenylmenthyl (2S,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate 
• 128114-52-3 8-Phenylmenthyl (2S,3R)-2-Hydroxy-5-methyl-3-nitro-hexanoate 
• 108794-01-0 (-)-8-phenylmenthyl (2S)-2-hydroxy-4-pentenoate 
• 108794-01-0 (R)-2-Hydroxy-pent-4-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 88292-43-7 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-2-hydroxyphenylacetate 
• 139005-51-9 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-2-hydroxyphenylacetate 
• 118466-99-2 (S)-3-Amino-2-triethylsilanyloxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 128114-54-5 (-)-8-Phenylmenthyl (2S,3R)-3-Amino-2-hydroxy-5-methyl-hexanoate 
• 128134-49-6 (-)-8-Phenylmenthyl (2S,3R)-3-Amino-5-methyl-2-((triethylsilyl)oxy)hexanoate 

Relevant academic research and scientific papers

Synthesis and X-ray crystal structure of (-)-calicheamicinone

Diels-Alder reaction between ketene acetal 3 and the β-nitroacrylate ester 12 of (-)-8-phenylmenthol gave optically pure ketone 17. This substance was modified in such a way as to remove the chiral auxiliary and afford the epimeric silyl ethers 20M and 20m. Following procedures worked out using racemic materials, both 20M and 20m were converted into optically pure (-)- calicheamicinone (1). This is a crystalline substance, and an X-ray structure determination was carried out.

Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivatives: Bronsted acid catalyzed aza-Diels-Alder reaction between cyclopentadiene and imino-acetates with two chiral auxiliaries

The cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl, and cyclopentadiene is described. The absolute configuration of all adducts formed was unequivocally assigned through NMR, specific optical rotation, and X-ray data of appropriated derivatives. Experimental results confirm the highly exo-selectivity for these aza-Diels-Alder reactions, single adducts being obtained from combinations of (8PM)-(R-PEA) and (8PNM)-(S-PEA).

An efficient method for preparation of chiral arylmenthol glyoxylates

Glyoxylates of three chiral alcohols were conveniently prepared by reaction of the alcohol with oxalyl chloride followed by reduction of the resulting alkoxy oxalyl chloride with tributyl- tin hydride. The products were isolated in 75-80% yield by straightforward flash chromatography.

ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY PURE S-ISOSERINE

KF-promoted addition of nitromethane on (-)-8-phenylmethyl glyoxylate monohydrate affords, after one purification, optically pure (-)S isoserine in about 50percent yield.