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

Base Information

• Chemical Name: 4-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester
• CAS No.: 852714-93-3
• Molecular Formula: C₃₂H₄₂NO₇P
• Molecular Weight: 583.662
• Mol file: 852714-93-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 4-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid 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:

Methyl-(4-{(R)-1-[2-oxo-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-ethyl]-allyl}-benzyl)-phosphinic acid tert-butyl ester (852714-92-2) + t-butyl iodoacetate (49827-15-8) → 4-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester (852714-93-3) + C32H42NO7P (852715-10-7)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.533333h; Cooling with acetone-dry ice;

Reference yield:

(tert-butoxy)[(4-bromophenyl)methyl]methylphosphin-1-one (852714-90-0) → 4-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester (852714-93-3)

Guidance literature:

Multi-step reaction with 3 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

With palladium diacetate; copper(I) thiophenolate; triethylamine; tris-(o-tolyl)phosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether;

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) → 4-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester (852714-93-3)

Guidance literature:

Multi-step reaction with 2 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

With copper(I) thiophenolate; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether;

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

1-bromomethyl-4-bromobenzene

(4S)-3-(1-oxo-2-propen-1-yl)-4-phenyl-1,3-oxazolidin-2-one

Downstream raw materials:

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

(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

C₂₄H₂₆NO₇P