(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran

Base Information

• Chemical Name: (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran
• CAS No.: 481725-20-6
• Molecular Formula: C₃₁H₄₈O₇SSi
• Molecular Weight: 592.869
• Mol file: 481725-20-6.mol

Synonyms:(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran

Chemical Property of (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran

There total 12 articles about (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran 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: 75.0%

(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]-2,5-dihydrofuran (481725-19-3) → (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran (481725-20-6)

Guidance literature:

With hydrogen; platinum on activated charcoal; In ethyl acetate; atmospheric pressure;

DOI:10.1016/S0957-4166(02)00334-8

Reference yield:

5-iodovaniline (5438-36-8) → (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran (481725-20-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 96 percent / cesium carbonate / dimethylformamide / 2 h / 50 °C

2.1: 91 percent / 2-methyl-2-butene; aq. sodium chlorite; NaH₂PO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

3.1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 18 h / 20 °C

4.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl₃; AIBN / 0.08 h / Heating

5.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C

6.1: 92 percent / imidazole / dimethylformamide / 20 °C

7.1: t-BuLi / pentane / 0.5 h / -78 °C

7.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C

8.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 °C

9.1: 67 percent / 450 °C / 0 Torr

10.1: 75 percent / H₂ / Pt/C / ethyl acetate / atmospheric pressure

With 1H-imidazole; dichloro-acetic acid; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; hydrogen; tert.-butyl lithium; 2-mercaptopyridine-1-oxide sodium salt; copper; sodium cyanoborohydride; caesium carbonate; platinum on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;

DOI:10.1016/S0957-4166(02)00334-8

Reference yield:

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) → (2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]tetrahydrofuran (481725-20-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

1.2: ClTi(O-i-Pr)3 / diethyl ether; pentane; hexane / -40 - 0 °C

1.3: 91 percent / tetrahydrofuran; diethyl ether; various solvents / 4.5 h / 0 - 20 °C

2.1: 78 percent / 4 Angstroem molecular sieves; 4-methoxymorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 5 h / 20 °C

3.1: t-BuLi / pentane / 0.5 h / -78 °C

3.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C

4.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 °C

5.1: 67 percent / 450 °C / 0 Torr

6.1: 75 percent / H₂ / Pt/C / ethyl acetate / atmospheric pressure

With dichloro-acetic acid; tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; hydrogen; tert.-butyl lithium; sodium cyanoborohydride; platinum on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; pentane;

DOI:10.1016/S0957-4166(02)00334-8

upstream raw materials:

(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfanyl)-4-propoxyphenyl]-2,5-dihydrofuran

5-iodovaniline

1-bromo-3,4,5-trimethoxybenzene

3-methoxy-4-n-propyloxy-5-iodobenzaldehyde

Downstream raw materials:

MK 287

(2S,5S)-2-(3',4',5'-trimethoxyphenyl)-5-[3-methoxy-5-(2'-t-butyldimethylsilyloxyethanesulfonyl)-4-propoxyphenyl]tetrahydrofuran

Refernces