(S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid

Base Information

• Chemical Name: (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid
• CAS No.: 1351987-35-3
• Molecular Formula: C₃₅H₄₈O₉
• Molecular Weight: 612.761
• Mol file: 1351987-35-3.mol

Synonyms:(S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid

Chemical Property of (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid

There total 29 articles about (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid 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: 98.0%

(S,E)-6-benzyl-1-tert-butyl-3-acetoxy-5-isopropyl-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)hex-2-enedioate (1351987-34-2) → (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid (1351987-35-3)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1002/adsc.201200934

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid (1351987-35-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere

1.2: 2.25 h / -40 °C

2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux

3.1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr

4.1: hydrogenchloride; 2-amino-2-hydroxymethyl-1,3-propanediol; water; HLAP / 48 h / 40 °C / Enzymatic reaction

4.2: 20 °C / pH 3.5

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere

5.2: 20 °C

6.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere

7.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux

8.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere

9.1: triethylamine / dmap / 3 h / Inert atmosphere

10.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; HLAP; water; hydrogen; triethylamine; 2-amino-2-hydroxymethyl-1,3-propanediol; trifluoroacetic acid; sodium iodide; lithium diisopropyl amide; dmap; palladium 10% on activated carbon; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; n-heptane; N,N-dimethyl acetamide; toluene; acetonitrile; benzene;

Reference yield:

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid (172900-71-9) → (S,E)-3-acetoxy-5-((benzyloxy)carbonyl)-2-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylhept-2-enoicacid (1351987-35-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere

1.2: 20 °C

2.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux

4.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere

5.1: triethylamine / dmap / 3 h / Inert atmosphere

6.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; triethylamine; trifluoroacetic acid; sodium iodide; dmap; In tetrahydrofuran; N,N-dimethyl acetamide; toluene; acetonitrile;

upstream raw materials:

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

(R)--4-(2-(iodomethyl)--3--methylbutyl)--1--methoxy-2--(3--methoxypropoxy)benzene

Downstream 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

{(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-furanidin-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester

(2S,3S,5S)-3-acetoxy-5-(benzyloxycarbonyl)-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-6-methylheptanoic acid

(2S,4S,5S,7S)-benzyl-4-acetoxy-5-(benzyloxycarbonylamino)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanoate