155795-48-5

Basic information

• Product Name: (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• Synonyms: (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS NO: 155795-48-5
• Molecular Weight: 410.491
• Mol File: 155795-48-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(155795-48-5)
• EPA Substance Registry System: (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester(155795-48-5)

Safety Data

• Hazardous Substances Data: 155795-48-5(Hazardous Substances Data)

Upstream product

• 65253-04-5 (-)-8-phenylmenthol 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 
• 122-52-1 triethyl phosphite 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 676345-33-8 (E)-Hex-2-enedioic acid 6-methyl ester 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 155897-15-7 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z)-3-[(2R)-3,4-dihydro-2H-pyran-2-yl]acrylate 
• 155897-13-5 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2E)-3-[(2R)-3,4-dihydro-2H-pyran-2-yl]acrylate 
• 155897-14-6 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z)-3-[(2S)-3,4-dihydro-2H-pyran-2-yl]acrylate 
• 155795-47-4 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2E)-3-[(2R)-3,4-dihydro-2H-pyran-2-yl]acrylate 

Relevant articles and documents

Lewis acid mediated asymmetric Diels-Alder reactions of chiral 2-phosphonoacrylates

2-Phosphonoacrylates containing four chiral alcohol auxiliaries were efficiently prepared and evaluated in Lewis acid mediated Diels-Alder reactions. Under the activation of SnCl4, all reactions performed in CH 2Cl2 at -65 °C exclusively afforded the endo (endo-to-carboxylate) cycloadducts with dr's ranging from 50:50 to >99:1. The best facial selectivity was obtained from the substrate bearing a (-)-phenylmenthyl group, to give adducts as (dr >99:1) or almost as (dr = 99:1) single diastereomers. Detailed strategies for the structural elucidation of the cycloadducts as well as a rationalization of the observed stereoselectivity are described.

Total synthesis of (-)-chokol A by an asymmetric domino Michael addition-Dieckmann cyclization

A convergent and asymmetric total synthesis of (-)-chokol A was accomplished in six steps starting from the α,β-unsaturated ester (E)-9 in an overall yield of 27% with an enantiomeric excess of 95%. The key step of this synthesis is the asymmetric tandem conjugate addition-Dieckmann cyclization of the higher-order cuprate 8 derived from vinyl bromide 7 with the α,β-unsaturated ester (E)-9. Georg Thieme Verlag Stuttgart.

Radical cyclizations - Synthesis of γ-lycorane

(+)-γ-Lycorane has been synthesized in ten steps from piperonylic alcohol. Two radical reactions were used successively to build the D and B rings. A formal synthesis of (+)-γ-lycorane was achieved via an optically active unsaturated aldehyde intermediate