(1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Base Information

Chemical Name:(1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
CAS No.:1420377-62-3
Molecular Formula:C₂₄H₃₃O₅P
Molecular Weight:432.497
Hs Code.:

Synonyms:(1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

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Chemical Property of (1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

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Technology Process of (1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

There total 5 articles about (1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1420376-53-9
2-(diethoxy-phosphoryl)acrylic acid (1R,2S)-2-phenyl-cyclohexyl ester

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 1420376-71-1
(1R,2S,4R)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

: 1420377-62-3
(1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -65 ℃; for 12h; Overall yield = 84 %; Overall yield = 277 mg; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.11.021

Reference yield:

: 98919-68-7
(1R,2S)-trans-2-phenylcyclohexanol

: 1420376-71-1
(1R,2S,4R)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

: 1420377-62-3
(1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap / toluene / 48 h / 115 °C / Inert atmosphere

2.1: potassium tert-butylate / dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere

2.2: 4 h / 60 °C / Inert atmosphere

3.1: dihydrogen peroxide / water; dichloromethane / 1.08 h / 20 °C / Inert atmosphere; Cooling with ice

4.1: tin(IV) chloride / dichloromethane / 12 h / -65 °C / Inert atmosphere

With dmap; potassium tert-butylate; dihydrogen peroxide; tin(IV) chloride; In dichloromethane; water; dimethyl sulfoxide; toluene; 4.1: |Diels-Alder Cycloaddition;
DOI:10.1016/j.tetasy.2012.11.021

Reference yield:

: 2-(diethoxy-phosphoryl)-2-phenylselanyl-propionic acid (1R,2S)-2-phenyl-cyclohexyl ester

: 1420376-71-1
(1R,2S,4R)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

: 1420377-62-3
(1S,2R,4S)-2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: dihydrogen peroxide / water; dichloromethane / 1.08 h / 20 °C / Inert atmosphere; Cooling with ice

2: tin(IV) chloride / dichloromethane / 12 h / -65 °C / Inert atmosphere

With dihydrogen peroxide; tin(IV) chloride; In dichloromethane; water; 2: |Diels-Alder Cycloaddition;
DOI:10.1016/j.tetasy.2012.11.021