2(5H)-Furanone, 3-[(2R)-9-[(2S,5S)-5-[(1S,4S)-4-[(2S,5R,6S)-6-decyltetrahydro-5-(meth oxymethoxy)-2H-pyran-2-yl]-1,4-bis(methoxymethoxy)butyl]tetrahydro-2- furanyl]-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-nonen-7-ynyl]-5-methyl- , (5S)-

Base Information

• Chemical Name: 2(5H)-Furanone, 3-[(2R)-9-[(2S,5S)-5-[(1S,4S)-4-[(2S,5R,6S)-6-decyltetrahydro-5-(meth oxymethoxy)-2H-pyran-2-yl]-1,4-bis(methoxymethoxy)butyl]tetrahydro-2- furanyl]-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-nonen-7-ynyl]-5-methyl- , (5S)-
• CAS No.: 500594-13-8
• Molecular Formula: C59H90O11Si
• Molecular Weight: 1003.44
• Mol file: 500594-13-8.mol

Synonyms:

Chemical Property of 2(5H)-Furanone, 3-[(2R)-9-[(2S,5S)-5-[(1S,4S)-4-[(2S,5R,6S)-6-decyltetrahydro-5-(meth oxymethoxy)-2H-pyran-2-yl]-1,4-bis(methoxymethoxy)butyl]tetrahydro-2- furanyl]-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-nonen-7-ynyl]-5-methyl- , (5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(5H)-Furanone, 3-[(2R)-9-[(2S,5S)-5-[(1S,4S)-4-[(2S,5R,6S)-6-decyltetrahydro-5-(meth oxymethoxy)-2H-pyran-2-yl]-1,4-bis(methoxymethoxy)butyl]tetrahydro-2- furanyl]-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-nonen-7-ynyl]-5-methyl- , (5S)-

There total 33 articles about 2(5H)-Furanone, 3-[(2R)-9-[(2S,5S)-5-[(1S,4S)-4-[(2S,5R,6S)-6-decyltetrahydro-5-(meth oxymethoxy)-2H-pyran-2-yl]-1,4-bis(methoxymethoxy)butyl]tetrahydro-2- furanyl]-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-nonen-7-ynyl]-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: 84.0%

3-[2-(tert-butyl-diphenyl-silanyloxy)-6-iodo-hex-5-enyl]-5-methyl-5H-furan-2-one (485322-57-4) + (2S,3R,6S)-6-[(1S,4S)-1,4-Bis-methoxymethoxy-4-((2S,5S)-5-prop-2-ynyl-tetrahydro-furan-2-yl)-butyl]-2-decyl-3-methoxymethoxy-tetrahydro-pyran (500593-98-6) → (S)-3-((E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2S,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-non-5-en-7-ynyl)-5-methyl-5H-furan-2-one (500594-13-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 0 - 20 ℃; for 1h;

DOI:10.1002/anie.200290038

Reference yield:

1,1,12,12-tetramethoxy-dodeca-4t,8t-diene (63284-80-0) → (S)-3-((E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2S,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-non-5-en-7-ynyl)-5-methyl-5H-furan-2-one (500594-13-8)

Guidance literature:

Multi-step reaction with 21 steps

1: AD-mix-α; MeSO2NH2; H2O / 2-methyl-propan-2-ol / 24 h / 0 °C

2: 10-camphorsulfonic acid / methanol / 3 h / -5 °C

3: 93 percent / NaH / tetrahydrofuran / 16 h / -15 - 20 °C

4: Zn(OTf)2 / 1,2-dichloro-ethane / 2 h / 50 °C

5: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

6: N-methylmorpholine / CH₂Cl₂ / 5 h / 20 °C

7: MeI; aq. NaHCO₃ / acetonitrile / 35 h / 20 °C

8: 87 percent / SmI₂ / methanol; tetrahydrofuran / 0.25 h / -5 °C

9: 93 percent / 10-camphorsulfonic acid / methanol / 30 h / 0 °C

10: 91 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 8 h / 0 - 40 °C

11: DIBAH / CH₂Cl₂ / 1 h / -78 °C

12: n-BuLi / tetrahydrofuran / 1 h / -15 °C

13: H₂ / Pd/C / methanol / 24 h / 20 °C / 750.06 Torr

14: i-Pr₂NEt / 1,2-dichloro-ethane / 1.5 h / 0 - 60 °C

15: 77 percent / aq. AcOH / 3 h / 20 - 40 °C

16: 85 percent / NaHMDS / tetrahydrofuran / 2 h / -15 - 20 °C

17: 78 percent / 4 Angstroem molecular sieves; O₂; t-BuO₂H / [Co(modp)2] / propan-2-ol / 5 h / 50 °C

18: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

19: hexamethylphosphoric acid triamide; tetrahydrofuran / 0.67 h / -78 °C

20: K₂CO₃ / methanol / 17 h / 20 °C

21: 84 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 1 h / 0 - 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis-triphenylphosphine-palladium(II) chloride; AD-mix-α; copper(l) iodide; n-butyllithium; samarium diiodide; methanesulfonamide; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; water; hydrogen; oxygen; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; palladium on activated charcoal; [Co(modp)2]; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1,2-dichloro-ethane; isopropyl alcohol; acetonitrile; tert-butyl alcohol; 1: Sharpless dihydroxylation / 6: hetero-Michael addition / 12: Wittig reaction;

DOI:10.1002/anie.200290038

Reference yield:

(4E,8E)-dodeca-4,8-dienedial (60391-93-7) → (S)-3-((E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2S,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-non-5-en-7-ynyl)-5-methyl-5H-furan-2-one (500594-13-8)

Guidance literature:

Multi-step reaction with 22 steps

1: 99 percent / 10-camphorsulfonic acid / methanol / 1 h / 20 °C

2: AD-mix-α; MeSO2NH2; H2O / 2-methyl-propan-2-ol / 24 h / 0 °C

3: 10-camphorsulfonic acid / methanol / 3 h / -5 °C

4: 93 percent / NaH / tetrahydrofuran / 16 h / -15 - 20 °C

5: Zn(OTf)2 / 1,2-dichloro-ethane / 2 h / 50 °C

6: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

7: N-methylmorpholine / CH₂Cl₂ / 5 h / 20 °C

8: MeI; aq. NaHCO₃ / acetonitrile / 35 h / 20 °C

9: 87 percent / SmI₂ / methanol; tetrahydrofuran / 0.25 h / -5 °C

10: 93 percent / 10-camphorsulfonic acid / methanol / 30 h / 0 °C

11: 91 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 8 h / 0 - 40 °C

12: DIBAH / CH₂Cl₂ / 1 h / -78 °C

13: n-BuLi / tetrahydrofuran / 1 h / -15 °C

14: H₂ / Pd/C / methanol / 24 h / 20 °C / 750.06 Torr

15: i-Pr₂NEt / 1,2-dichloro-ethane / 1.5 h / 0 - 60 °C

16: 77 percent / aq. AcOH / 3 h / 20 - 40 °C

17: 85 percent / NaHMDS / tetrahydrofuran / 2 h / -15 - 20 °C

18: 78 percent / 4 Angstroem molecular sieves; O₂; t-BuO₂H / [Co(modp)2] / propan-2-ol / 5 h / 50 °C

19: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

20: hexamethylphosphoric acid triamide; tetrahydrofuran / 0.67 h / -78 °C

21: K₂CO₃ / methanol / 17 h / 20 °C

22: 84 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 1 h / 0 - 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; bis-triphenylphosphine-palladium(II) chloride; AD-mix-α; copper(l) iodide; n-butyllithium; samarium diiodide; methanesulfonamide; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; water; hydrogen; oxygen; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; palladium on activated charcoal; [Co(modp)2]; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1,2-dichloro-ethane; isopropyl alcohol; acetonitrile; tert-butyl alcohol; 2: Sharpless dihydroxylation / 7: hetero-Michael addition / 13: Wittig reaction;

DOI:10.1002/anie.200290038

upstream raw materials:

3-[2-(tert-butyl-diphenyl-silanyloxy)-6-iodo-hex-5-enyl]-5-methyl-5H-furan-2-one

(2S,3R,6S)-6-[(1S,4S)-1,4-Bis-methoxymethoxy-4-((2S,5S)-5-prop-2-ynyl-tetrahydro-furan-2-yl)-butyl]-2-decyl-3-methoxymethoxy-tetrahydro-pyran

1,1,12,12-tetramethoxy-dodeca-4t,8t-diene

(4E,8E)-dodeca-4,8-dienedial