(S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
• CAS No.: 862603-47-2
• Molecular Formula: C₄₉H₈₄O₆SSi
• Molecular Weight: 829.354

Synonyms:(S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property of (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property:

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Technology Process of (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

There total 40 articles about (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-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:

(S)-1-((2S,4S)-2-Phenyl-[1,3]dioxan-4-yl)-propane-1,3-diol (862603-59-6) → (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (862603-47-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: Et₃N / CH₂Cl₂ / 12 h / 0 °C

2.1: N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

3.1: NaI / acetone / 3 h / Heating

4.1: n-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

5.1: sym-collidine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

5.2: aq. KOAc / acetonitrile / 1.5 h / 0 °C

6.1: Mg / tetrahydrofuran / 0 °C

6.2: tetrahydrofuran / 0 - 20 °C

7.1: imidazole / CH₂Cl₂; dimethylformamide / 18 h

8.1: H₂ / Pd/C / ethyl acetate / 18 h

9.1: Et₃N / CH₂Cl₂ / 12 h / 0 °C

10.1: N-methylmorpholine / CH₂Cl₂ / 36 h / 20 °C

11.1: NaI / acetone / 3 h / Heating

12.1: N-Bu₃SnH; Et₃B; air / toluene; hexane / 0.5 h / -20 °C

13.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.5 h / 0 °C

13.2: aq. KOAc / acetonitrile / 2 h / 0 °C

14.1: MgBr₂ / CH₂Cl₂; diethyl ether / 2 h / 20 °C

15.1: second-generation Grubbs catalyst / CH₂Cl₂ / 20 h / 45 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,4,6-trimethyl-pyridine; air; triethyl borane; hydrogen; tri-n-butyl-tin hydride; magnesium; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Pummerer rearrangement / 6.2: Grignard reaction / 13.1: Pummerer rearrangement;

DOI:10.1021/ja0526867

Reference yield:

(2R,5S)-5-((2S,4S)-2-Phenyl-[1,3]dioxan-4-yl)-tetrahydro-furan-2-carbaldehyde (862602-96-8) → (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (862603-47-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Mg / tetrahydrofuran / 0 °C

1.2: tetrahydrofuran / 0 - 20 °C

2.1: imidazole / CH₂Cl₂; dimethylformamide / 18 h

3.1: H₂ / Pd/C / ethyl acetate / 18 h

4.1: Et₃N / CH₂Cl₂ / 12 h / 0 °C

5.1: N-methylmorpholine / CH₂Cl₂ / 36 h / 20 °C

6.1: NaI / acetone / 3 h / Heating

7.1: N-Bu₃SnH; Et₃B; air / toluene; hexane / 0.5 h / -20 °C

8.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.5 h / 0 °C

8.2: aq. KOAc / acetonitrile / 2 h / 0 °C

9.1: MgBr₂ / CH₂Cl₂; diethyl ether / 2 h / 20 °C

10.1: second-generation Grubbs catalyst / CH₂Cl₂ / 20 h / 45 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; air; triethyl borane; hydrogen; tri-n-butyl-tin hydride; magnesium; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.2: Grignard reaction / 8.1: Pummerer rearrangement;

DOI:10.1021/ja0526867

Reference yield:

(S)-1-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-propane-1,3-diol (862603-72-3) → (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (862603-47-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

2.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

3.1: 93 percent / NaI / acetone / 9 h / Heating

4.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

5.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

5.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

6.1: Mg / diethyl ether / -78 °C

6.2: diethyl ether / 2 h / -78 °C

7.1: 99 percent / imidazole / CH₂Cl₂; dimethylformamide / 8 h / 20 °C

8.1: 98 percent / H₂ / Pd/C / ethyl acetate / 14 h

9.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: MgBr₂ / CH₂Cl₂; diethyl ether / 2 h / 20 °C

11.1: second-generation Grubbs catalyst / CH₂Cl₂ / 20 h / 45 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; triethyl borane; hydrogen; tri-n-butyl-tin hydride; magnesium; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; palladium on activated charcoal; In diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Pummerer rearrangement / 9.1: Swern oxidtion;

DOI:10.1021/ja0526867

upstream raw materials:

(S)-5-methyl-3-(phenylthio)-3-(10-undecenyl)dihydrofuran-2(3H)-one

(R)-1-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-but-3-en-1-ol

(S)-1-((2S,4S)-2-Phenyl-[1,3]dioxan-4-yl)-propane-1,3-diol

(2R,5S)-5-((2S,4S)-2-Phenyl-[1,3]dioxan-4-yl)-tetrahydro-furan-2-carbaldehyde

Downstream raw materials:

(S)-3-((R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

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