(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

Base Information

Chemical Name:(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
CAS No.:1420377-65-6
Molecular Formula:C₂₂H₃₇O₅P
Molecular Weight:412.507
Hs Code.:

Synonyms:(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

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Chemical Property of (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

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Technology Process of (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

There total 4 articles about (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate 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:

: 1420376-59-5
2-(diethoxy-phosphoryl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

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

: 1420376-77-7
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2S,4R)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

: 1420377-65-6
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -65 ℃; for 12h; Overall yield = 87 %; Overall yield = 415 mg; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.11.021

Reference yield:

: 2216-51-5
(-)-menthol

: 1420377-65-6
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

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:

: 141540-20-7
(diethoxy-phosphoryl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

: 1420377-65-6
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 4 h / 60 °C / Inert atmosphere

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

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

With potassium tert-butylate; dihydrogen peroxide; tin(IV) chloride; In dichloromethane; water; dimethyl sulfoxide; 3.1: |Diels-Alder Cycloaddition;
DOI:10.1016/j.tetasy.2012.11.021