(4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester

Base Information

• Chemical Name: (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester
• CAS No.: 510773-82-7
• Molecular Formula: C₃₁H₄₁N₄O₇P
• Molecular Weight: 612.663
• Mol file: 510773-82-7.mol

Synonyms:(4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester

Chemical Property of (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester

There total 6 articles about (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-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:

1-((4S)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl))-(2S,3R)-2-azido-6-hydroxy-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hexan-1-one (525575-17-1) → (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester (510773-82-7)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(02)01421-7

Reference yield:

3-(3-(4-((bis(tert-butyl)phosphono)methyl)phenyl)prop-2-enoyl)-4(S)-benzyl-1,3-oxazolidin-2-one → (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester (510773-82-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / CuBr*SMe₂ / tetrahydrofuran / 2.5 h / -78 °C

2.1: BH₃ / tetrahydrofuran / 1 h / 0 °C

2.2: 90 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 3 h / 20 °C

3.1: 82 percent / imidazole / dimethylformamide / 20 °C

4.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 °C

4.2: 35 percent / trisyl azide / tetrahydrofuran / 0.03 h / -78 °C

5.1: 87 percent / HF*pyridine / tetrahydrofuran / 0 - 20 °C

6.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; borane; potassium hexamethylsilazane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Michael addition / 6.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01421-7

Reference yield:

(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one (510773-80-5) → (4-{(R)-1-[(S)-1-Azido-2-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-4-oxo-butyl}-benzyl)-phosphonic acid di-tert-butyl ester (510773-82-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BH₃ / tetrahydrofuran / 1 h / 0 °C

1.2: 90 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 3 h / 20 °C

2.1: 82 percent / imidazole / dimethylformamide / 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 °C

3.2: 35 percent / trisyl azide / tetrahydrofuran / 0.03 h / -78 °C

4.1: 87 percent / HF*pyridine / tetrahydrofuran / 0 - 20 °C

5.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; borane; potassium hexamethylsilazane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)01421-7

upstream raw materials:

1-((4S)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl))-(2S,3R)-2-azido-6-hydroxy-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hexan-1-one

(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one

(4S)-3-((3S)-6-hydroxy-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one

(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one

Downstream raw materials:

2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

{2-{1-[2-carbamoyl-1-(3-naphthalen-1-yl-propylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-piperidin-1-yl}-oxo-acetic acid tert-butyl ester

(2S,3R)-1-((fluoren-9-ylmethyl)oxycarbonyl)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)piperidine-2-carboxylic acid

methyl (2S,3R)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)piperidine-2-carboxylate