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

Base Information

• Chemical Name: (4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one
• CAS No.: 510773-80-5
• Molecular Formula: C₃₁H₄₂NO₆P
• Molecular Weight: 555.651
• Mol file: 510773-80-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one 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: 80.0%

3-(3-(4-((bis(tert-butyl)phosphono)methyl)phenyl)prop-2-enoyl)-4(S)-benzyl-1,3-oxazolidin-2-one + allylmagnesium bromide (1730-25-2) → (4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one (510773-80-5)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 2.5h;

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

Reference yield: 90.0%

(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one (510773-80-5) → (4S)-3-((3S)-6-hydroxy-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one (510773-81-6)

Guidance literature:

(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)hex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one; With borane; In tetrahydrofuran; at 0 ℃; for 1h;

With sodium perborate; In tetrahydrofuran; water; at 20 ℃; for 3h;

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) → methyl (2S,3R)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)piperidine-2-carboxylate (510773-83-8)

Guidance literature:

Multi-step reaction with 6 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

6.1: 17 mg / H₂ / 10 percent Pd-C / 20 °C / 2068.59 Torr

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

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

upstream raw materials:

allylmagnesium bromide

Downstream raw materials:

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

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

(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

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