(S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one

Base Information

• Chemical Name: (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one
• CAS No.: 528598-62-1
• Molecular Formula: C₅₇H₉₂O₁₀Si
• Molecular Weight: 965.437
• Mol file: 528598-62-1.mol

Synonyms:(S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one

Chemical Property of (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one

There total 24 articles about (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one 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: 69.0%

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal (198541-55-8) + [(3S,8R)-8-((2R,5R,6R)-6-Dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-3,8-bis-methoxymethoxy-octyl]-triphenyl-phosphonium; iodide → (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one (528598-62-1)

Guidance literature:

[(3S,8R)-8-((2R,5R,6R)-6-Dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-3,8-bis-methoxymethoxy-octyl]-triphenyl-phosphonium; iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃;

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ol034323m

Reference yield:

(S)-1-Benzyloxy-hex-5-yn-3-ol → (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one (528598-62-1)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 0 °C

2.1: n-BuLi / tetrahydrofuran

2.2: N,N-dimethylpropyleneurea / tetrahydrofuran / -15 °C

3.1: TBAF / tetrahydrofuran / 20 °C

4.1: 95 percent / H₂ / (Ph₃P)3RhCl / benzene / 20 °C

5.1: Et₃N / CH₂Cl₂ / -15 °C

6.1: CuBr / diethyl ether / -15 - 20 °C

7.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

7.2: 76 percent / CSA / methanol / 0 °C

8.1: 98 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

9.1: 97 percent / Zn(OTf)2 / 1,2-dichloro-ethane / 50 °C

10.1: 94 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

11.1: 92 percent / MeI; aq. NaHCO₃ / acetonitrile / 0 - 20 °C

12.1: 95 percent / SmI₂ / methanol; tetrahydrofuran / 0 °C

13.1: 97 percent / aq. NaOH / ethanol / 20 °C

14.1: 92 percent / PPh₃; DEAD / tetrahydrofuran / 0 °C

15.1: DIBAL / CH₂Cl₂ / -78 °C

15.2: 87 percent / n-BuLi / tetrahydrofuran / -15 °C

16.1: i-Pr₂NEt / 1,2-dichloro-ethane / 0 - 50 °C

17.1: H₂ / 10 percent Pd/C / ethanol / 20 °C

18.1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

19.1: i-Pr₂NEt / 1,2-dichloro-ethane / 0 - 50 °C

20.1: TBAF / tetrahydrofuran / 20 °C

21.1: 98 percent / I₂; PPh₃; imidazole / benzene / 0 °C

22.1: 93 percent / acetonitrile / 60 °C

23.1: NaHMDS / tetrahydrofuran / 0 °C

23.2: 69 percent / tetrahydrofuran / -78 °C

With 4-methyl-morpholine; 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(I) bromide; diethylazodicarboxylate; methyl iodide; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene; 15.2: Wittig reaction / 23.2: Wittig reaction;

DOI:10.1021/ol034323m

Reference yield:

(S)-1-Benzyloxy-6-trimethylsilanyl-hex-5-yn-3-ol → (S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one (528598-62-1)

Guidance literature:

Multi-step reaction with 24 steps

1.1: K₂CO₃; MeOH / 20 °C

2.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 0 °C

3.1: n-BuLi / tetrahydrofuran

3.2: N,N-dimethylpropyleneurea / tetrahydrofuran / -15 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: 95 percent / H₂ / (Ph₃P)3RhCl / benzene / 20 °C

6.1: Et₃N / CH₂Cl₂ / -15 °C

7.1: CuBr / diethyl ether / -15 - 20 °C

8.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

8.2: 76 percent / CSA / methanol / 0 °C

9.1: 98 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

10.1: 97 percent / Zn(OTf)2 / 1,2-dichloro-ethane / 50 °C

11.1: 94 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

12.1: 92 percent / MeI; aq. NaHCO₃ / acetonitrile / 0 - 20 °C

13.1: 95 percent / SmI₂ / methanol; tetrahydrofuran / 0 °C

14.1: 97 percent / aq. NaOH / ethanol / 20 °C

15.1: 92 percent / PPh₃; DEAD / tetrahydrofuran / 0 °C

16.1: DIBAL / CH₂Cl₂ / -78 °C

16.2: 87 percent / n-BuLi / tetrahydrofuran / -15 °C

17.1: i-Pr₂NEt / 1,2-dichloro-ethane / 0 - 50 °C

18.1: H₂ / 10 percent Pd/C / ethanol / 20 °C

19.1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

20.1: i-Pr₂NEt / 1,2-dichloro-ethane / 0 - 50 °C

21.1: TBAF / tetrahydrofuran / 20 °C

22.1: 98 percent / I₂; PPh₃; imidazole / benzene / 0 °C

23.1: 93 percent / acetonitrile / 60 °C

24.1: NaHMDS / tetrahydrofuran / 0 °C

24.2: 69 percent / tetrahydrofuran / -78 °C

With 4-methyl-morpholine; 1H-imidazole; methanol; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(I) bromide; diethylazodicarboxylate; methyl iodide; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene; 16.2: Wittig reaction / 24.2: Wittig reaction;

DOI:10.1021/ol034323m

upstream raw materials:

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

1-{[(S)-1-(Bbenzyloxy)hex-5-yn-3-yloxy]methyl}benzene

[(4R,5R)-5-((S)-5,7-Bis-benzyloxy-heptyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

[(4R,5R)-5-((S)-5,7-Bis-benzyloxy-hept-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Downstream raw materials:

(S)-3-[(2R,8R,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridecyl]-5-methyl-5H-furan-2-one