(Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester

Base Information

• Chemical Name: (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester
• CAS No.: 934008-41-0
• Molecular Formula: C₂₄H₃₄Cl₃NO₆S
• Molecular Weight: 570.962
• Mol file: 934008-41-0.mol

Synonyms:(Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester

Chemical Property of (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester

There total 7 articles about (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) 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: 52.0%

(Z)-7-[(E)-(R)-2-methyl-propane-2-sulfinylimino]-hept-4-enoic acid 2,2,2-trichloro-ethyl ester (934008-40-9) + (4-methoxyphenyl)methyl propanoate (7549-33-9) → (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester (934008-41-0)

Guidance literature:

(4-methoxyphenyl)methyl propanoate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With triisopropoxytitanium(IV) chloride; titanium tetrachloride; In tetrahydrofuran; hexane; at -78 ℃; for 0.833333h;

(Z)-7-[(E)-(R)-2-methyl-propane-2-sulfinylimino]-hept-4-enoic acid 2,2,2-trichloro-ethyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 3.5h;

DOI:10.1021/ol070046y

Reference yield:

4-pentynoic acid 2,2,2-trichloro-ethyl ester (913055-64-8) → (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester (934008-41-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CuCl / dimethylformamide / 0.17 h

1.2: 98 percent / potassium carbonate; Bu₄NI / dimethylformamide / 36 h / 20 °C

2.1: 82 percent / OsO₄; N-methylmorpholine N-oxide / H₂O; tetrahydrofuran; acetone / 13 h

3.1: 96 percent / hydrogen / Lindlar catalyst / 4 h

4.1: 96 percent / NaIO₄ / CH₂Cl₂; H₂O / 0.67 h / 20 °C

5.1: 58 percent / CuSO₄ / CH₂Cl₂ / 3 h / 20 °C

6.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: TiCl₄; TiCl(O-iPr)3 / tetrahydrofuran; hexane / 0.83 h / -78 °C

6.3: 52 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

With sodium periodate; osmium(VIII) oxide; hydrogen; copper(II) sulfate; 4-methylmorpholine N-oxide; copper(l) chloride; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol070046y

Reference yield:

oct-7-en-4-ynoic acid 2,2,2-trichloro-ethyl ester (934008-36-3) → (Z)-(7R,8S)-8-methyl-7-((R)-2-methyl-propane-2-sulfinylamino)-non-4-enedioc acid 9-(4-methoxy-benzyl) ester 1-(2,2,2-trichloro-ethyl) ester (934008-41-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / OsO₄; N-methylmorpholine N-oxide / H₂O; tetrahydrofuran; acetone / 13 h

2.1: 96 percent / hydrogen / Lindlar catalyst / 4 h

3.1: 96 percent / NaIO₄ / CH₂Cl₂; H₂O / 0.67 h / 20 °C

4.1: 58 percent / CuSO₄ / CH₂Cl₂ / 3 h / 20 °C

5.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: TiCl₄; TiCl(O-iPr)3 / tetrahydrofuran; hexane / 0.83 h / -78 °C

5.3: 52 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

With sodium periodate; osmium(VIII) oxide; hydrogen; copper(II) sulfate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; acetone;

DOI:10.1021/ol070046y

upstream raw materials:

(Z)-7-[(E)-(R)-2-methyl-propane-2-sulfinylimino]-hept-4-enoic acid 2,2,2-trichloro-ethyl ester

(4-methoxyphenyl)methyl propanoate

4-pentynoic acid 2,2,2-trichloro-ethyl ester

(Z)-7-oxo-hept-4-enoic acid 2,2,2-trichloro-ethyl ester

Refernces