(3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid

Base Information

• Chemical Name: (3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid
• CAS No.: 495403-75-3
• Molecular Formula: C₂₁H₃₃O₅P
• Molecular Weight: 396.464
• Mol file: 495403-75-3.mol

Synonyms:(3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid

Chemical Property of (3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid

There total 1 articles about (3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid 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: 90.0%

[4-[(1S)-[2-[2-oxo-2-[(4S)-2-oxo-4-phenyl-3-oxazolidinyl]ethyl]-3-butenyl]phenyl]methyl]-phosphonoic acid bis(tert-butyl) ester → (3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid (495403-75-3)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm0203635

Reference yield: 79.0%

(2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (401810-35-3) + (3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid (495403-75-3) → (3S)-N-{[N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)carbamoyl]cyclohexyl}-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enamide (495403-84-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm0203635

Reference yield:

(3S)-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoic acid (495403-75-3) → 2-[(9S,13S,18S)-8,11,21-triaza-18-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13-(naphthylmethyl)-7,10,20-trioxospiro[5.15]henicos-15-en-9-yl]acetamide (495403-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / HOBt; EDCI / dimethylformamide / 20 °C

2: 77 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 60 h / Heating

With Grubbs catalyst first generation; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0203635

Downstream raw materials:

(3S)-N-{[N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)carbamoyl]cyclohexyl}-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enamide

2-[(9S,13S,18S)-8,11,21-triaza-18-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13-(naphthylmethyl)-7,10,20-trioxospiro[5.15]henicos-15-en-9-yl]acetamide