2(5H)-Furanone, 3-[(2R,8R,13R)-13-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[(2R,5R,6R )-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-dodecyltetrahydro-2H-pyran- 2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl]-5-methyl-, (5S)-

Base Information

• Chemical Name: 2(5H)-Furanone, 3-[(2R,8R,13R)-13-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[(2R,5R,6R )-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-dodecyltetrahydro-2H-pyran- 2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl]-5-methyl-, (5S)-
• CAS No.: 837428-50-9
• Molecular Formula: C62H108O7Si3
• Molecular Weight: 1049.79
• Mol file: 837428-50-9.mol

Synonyms:

Chemical Property of 2(5H)-Furanone, 3-[(2R,8R,13R)-13-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[(2R,5R,6R )-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-dodecyltetrahydro-2H-pyran- 2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl]-5-methyl-, (5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(5H)-Furanone, 3-[(2R,8R,13R)-13-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[(2R,5R,6R )-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-dodecyltetrahydro-2H-pyran- 2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl]-5-methyl-, (5S)-

There total 32 articles about 2(5H)-Furanone, 3-[(2R,8R,13R)-13-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[(2R,5R,6R )-5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-dodecyltetrahydro-2H-pyran- 2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl]-5-methyl-, (5S)- 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: 85.0%

(5S)-3-{(2R,8R,11E,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-{(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(E)-dodec-2-en-1-yl]tetrahydro-2H-pyran-2-yl}-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridec-11-en-9-yn-1-yl}-5-methylfuran-2(5H)-one (837428-44-1) → (5S)-3-{(2R,8R,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-[(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-dodecyltetrahydro-2H-pyran-2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl}-5-methylfuran-2(5H)-one (837428-50-9)

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; for 4h; Heating;

DOI:10.1021/ol0479242

Reference yield:

(5S)-3-{(2R,8R)-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]dec-9-yn-1-yl}-5-methylfuran-2(5H)-one (837428-22-5) → (5S)-3-{(2R,8R,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-[(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-dodecyltetrahydro-2H-pyran-2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl}-5-methylfuran-2(5H)-one (837428-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: (PPh₃)2PdCl₂; CuI; Et₃N / 2.5 h / 20 °C

2: tosylhydrazine; aq. NaOAc / 1,2-dimethoxy-ethane / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium acetate; triethylamine; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; 1: Sonogashira coupling;

DOI:10.1021/jo052233k

Reference yield:

(S)-4-Hydroxy-3-[(2R,8R)-8-hydroxy-2-(2-trimethylsilanyl-ethoxy)-dec-9-ynyl]-5-methyl-dihydro-furan-2-one (881663-87-2) → (5S)-3-{(2R,8R,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-[(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-dodecyltetrahydro-2H-pyran-2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl}-5-methylfuran-2(5H)-one (837428-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 33 mg / aq. NaHCO₃ / CH₂Cl₂; tetrahydrofuran / 3 h / 20 °C

3: (PPh₃)2PdCl₂; CuI; Et₃N / 2.5 h / 20 °C

4: tosylhydrazine; aq. NaOAc / 1,2-dimethoxy-ethane / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium acetate; sodium hydrogencarbonate; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 3: Sonogashira coupling;

DOI:10.1021/jo052233k

upstream raw materials:

(5S)-3-{(2R,8R,11E,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-{(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(E)-dodec-2-en-1-yl]tetrahydro-2H-pyran-2-yl}-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridec-11-en-9-yn-1-yl}-5-methylfuran-2(5H)-one

(2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran

decyltriphenylphosphonium bromide

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial