2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester

Base Information

• Chemical Name: 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester
• CAS No.: 857083-13-7
• Molecular Formula: C₂₃H₃₅O₆P
• Molecular Weight: 438.501
• Mol file: 857083-13-7.mol

Synonyms:2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester

Chemical Property of 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester

There total 6 articles about 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl 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:

(3S,4S)-4-[4-(Hydroxy-methyl-phosphinoylmethyl)-phenyl]-3-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester → 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester (857083-13-7)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/jm050059m

Reference yield:

(tert-butoxy)[(4-bromophenyl)methyl]methylphosphin-1-one (852714-90-0) → 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester (857083-13-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 73 percent / tri-O-tolylphosphine; Pd(OAc)2; Et₃N / 12 h / Heating

2.1: PhSCu / diethyl ether; tetrahydrofuran / -40 °C

2.2: 76 percent / diethyl ether; tetrahydrofuran / 1.1 h / -40 °C

3.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 61 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

4.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

5.1: aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

With palladium diacetate; lithium hydroxide; dihydrogen peroxide; copper(I) thiophenolate; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm050059m

Reference yield:

Methyl-{4-[(E)-3-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-propenyl]-benzyl}-phosphinic acid tert-butyl ester (852714-91-1) → 2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester (857083-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: PhSCu / diethyl ether; tetrahydrofuran / -40 °C

1.2: 76 percent / diethyl ether; tetrahydrofuran / 1.1 h / -40 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 61 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

3.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

4.1: aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

With lithium hydroxide; dihydrogen peroxide; copper(I) thiophenolate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm050059m

upstream raw materials:

(tert-butoxy)[(4-bromophenyl)methyl]methylphosphin-1-one

Methyl-{4-[(E)-3-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-propenyl]-benzyl}-phosphinic acid tert-butyl ester

Methyl-(4-{(R)-1-[2-oxo-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-ethyl]-allyl}-benzyl)-phosphinic acid tert-butyl ester

4-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester

Downstream raw materials:

(3S,4S)-4-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester

[(E)-(9S,10S,14R,18S)-10-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-18-carbamoylmethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-9-yl]-acetic acid tert-butyl ester