Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester
• CAS No.: 862603-02-9
• Molecular Formula: C₄₀H₆₄O₇S₂Si
• Molecular Weight: 749.161

Synonyms:Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester

There total 15 articles about Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester 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) → Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester (862603-02-9)

Guidance literature:

Multi-step reaction with 10 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

With 4-methyl-morpholine; 1H-imidazole; 2,4,6-trimethyl-pyridine; triethyl borane; hydrogen; tri-n-butyl-tin hydride; magnesium; triethylamine; trifluoroacetic anhydride; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Pummerer rearrangement / 6.2: Grignard reaction;

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) → Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester (862603-02-9)

Guidance literature:

Multi-step reaction with 5 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

With 4-methyl-morpholine; 1H-imidazole; hydrogen; magnesium; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.2: Grignard reaction;

DOI:10.1021/ja0526867

Reference yield:

6-(tert-butyl-diphenyl-silanyloxy)-hex-3-enoic acid methyl ester (862603-51-8) → Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester (862603-02-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

2.1: LiAlH₄ / tetrahydrofuran / -78 - 20 °C

3.1: (+/-)-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

4.1: Bu₄NF / tetrahydrofuran / 3 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 12 h / 0 °C

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

7.1: NaI / acetone / 3 h / Heating

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

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

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

10.1: Mg / tetrahydrofuran / 0 °C

10.2: tetrahydrofuran / 0 - 20 °C

11.1: imidazole / CH₂Cl₂; dimethylformamide / 18 h

12.1: H₂ / Pd/C / ethyl acetate / 18 h

13.1: Et₃N / CH₂Cl₂ / 12 h / 0 °C

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

With 4-methyl-morpholine; 1H-imidazole; 2,4,6-trimethyl-pyridine; AD-mix-α; lithium aluminium tetrahydride; triethyl borane; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; magnesium; triethylamine; trifluoroacetic anhydride; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 9.1: Pummerer rearrangement / 10.2: Grignard reaction;

DOI:10.1021/ja0526867

upstream raw materials:

Toluene-4-sulfonic acid (S)-3-{(2S,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-tetrahydro-furan-2-yl}-3-hydroxy-propyl ester

(+)-(R)_S-ethynyl-p-tolylsulfoxide

(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-((2R,13R)-2-(tert-Butyl-dimethyl-silanyloxy)-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

(S)-3-((E)-(2R,13R)-2-(tert-Butyl-dimethyl-silanyloxy)-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

(S)-3-((2R,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-11-hydroxy-undecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

(S)-3-((E)-(2R,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-11-hydroxy-undec-8-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

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