(1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester
• CAS No.: 173337-63-8
• Molecular Formula: C₃₄H₆₀N₂O₇
• Molecular Weight: 608.86
• Mol file: 173337-63-8.mol

Synonyms:(1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

Chemical Property of (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

There total 14 articles about (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic 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: 81.0%

(4S,5S,2'S,2''S)-5-(2'-butylcarbamoyl-3-methylbutyl)-4-{2''-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester → (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester (173337-63-8)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 20 ℃; for 18h;

DOI:10.1021/jm070316i

Reference yield: 58.0%

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate (866030-35-5) + N-butylamine (109-73-9,85404-21-3) → (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester (173337-63-8)

Guidance literature:

With trimethylaluminum; In dichloromethane; toluene; at 20 ℃; for 20h;

DOI:10.1021/jo060296c

Reference yield:

methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate (900811-40-7) → (1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester (173337-63-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C

2.1: 94 percent / EDCI / CH₂Cl₂ / 3.5 h / 0 °C

3.1: 67 percent / t-BuOH; SmI₂ / tetrahydrofuran / 144 h / -78 °C

4.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C

5.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

5.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C

6.1: PCl₅ / CH₂Cl₂ / 2.5 h / 0 °C

6.2: 39 mg / H₂ / Pd/C / ethanol / 48 h

7.1: 63 percent / Et₃N / tetrahydrofuran / 18 h / 20 °C

8.1: 58 percent / trimethylaluminum / CH₂Cl₂; toluene / 20 h / 20 °C

With sodium hydroxide; samarium diiodide; (S)-alpine-hydride; phosphorus pentachloride; trimethylaluminum; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hexamethyldisilazane; tert-butyl alcohol; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.2: aldol reaction;

DOI:10.1021/jo060296c

upstream raw materials:

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

N-butylamine

(5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-aminopentyl]-3-(1-methylethyl)-2(3H)-furanone

methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate