(S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
• CAS No.: 879290-52-5
• Molecular Formula: C₆₁H₁₁₄O₇SSi₃
• Molecular Weight: 1075.89

Synonyms:(S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property of (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

There total 26 articles about (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-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: 87.0%

(2R,3R,5S,2'S,5'S)-3-(tert-Butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hexyl]-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl (879290-46-7) + (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one (184435-75-4) → (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (879290-52-5)

Guidance literature:

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃; for 0.5h;

(2R,3R,5S,2'S,5'S)-3-(tert-Butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hexyl]-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 15h;

DOI:10.1021/jo052073c

Reference yield:

(E)-Henicos-3-en-1-ol (879290-72-9) → (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (879290-52-5)

Guidance literature:

Multi-step reaction with 22 steps

1.1: NaH; TBAI / tetrahydrofuran / 18 h / 60 °C

2.1: 92 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 20 h / 0 °C

3.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 3 h / 20 °C

4.1: 78 percent / DDQ; phosphate buffer / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

5.1: 96 percent / bisacetoxyiodobenzene; TEMPO / CH₂Cl₂ / 2 h / 20 °C

6.1: 91 percent / tetrahydrofuran / 16 h / Heating

7.1: 89 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / 0 °C

8.1: 73 percent / D-(-)-DET; Ti(OiPr)4; t-BuOOH / CH₂Cl₂; toluene / 2.75 h / -30 - -20 °C

9.1: 94 percent / tributylphosphine; triethylamine / 6 h / 0 - 20 °C

10.1: 56 percent / BF₃*OEt₂ / diethyl ether / 5 h / 0 - 20 °C

11.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 100 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

14.1: 532 mg / water; NaHCO₃ / acetonitrile / 16 h / 20 °C

15.1: t-BuLi / diethyl ether; pentane / 0.25 h / -100 - -90 °C

15.2: MgBr₂*OEt₂ / diethyl ether; pentane / 1 h / -90 - 0 °C

15.3: 85 percent / MgBr₂*OEt₂ / diethyl ether; pentane / -40 °C

16.1: 73 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 16 h / 0 °C

17.1: PPTS / CH₂Cl₂ / 0.08 h / 20 °C

17.2: BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / 20 °C

17.3: 99 percent / 2,6-lutidine

18.1: MeOH; K₂CO₃ / 17 h / 20 °C

19.1: 189 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

20.1: 92 percent / H₂ / Pd/C / ethyl acetate; propan-2-ol / 1 h / 20 °C / 760 Torr

21.1: 87 percent / triphenylphosphine; imidazole; iodine / toluene / 1 h / 20 °C

22.1: LDA / tetrahydrofuran / 0.5 h / -78 - 0 °C

22.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 15 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; AD-mix-α; phosphate buffer; diethyl (2S,3S)-tartrate; tributylphosphine; methanesulfonamide; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; water; hydrogen; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; potassium osmate(VI); palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; pentane; 2.1: Sharpless asymmetric dihydroxylation / 6.1: Wittig olefination / 8.1: Sharpless asymmetric epoxidation / 13.1: Pummerer rearrangement / 16.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo052073c

Reference yield:

heneicos-3-yn-1-ol (879290-35-4) → (S)-3-((S)-6-(tert-Butyl-dimethyl-silanyloxy)-6-{(2S,5S,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one (879290-52-5)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 87 percent / LAH / bis-(2-methoxy-ethyl) ether / 17 h / 125 °C

2.1: NaH; TBAI / tetrahydrofuran / 18 h / 60 °C

3.1: 92 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 20 h / 0 °C

4.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 3 h / 20 °C

5.1: 78 percent / DDQ; phosphate buffer / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

6.1: 96 percent / bisacetoxyiodobenzene; TEMPO / CH₂Cl₂ / 2 h / 20 °C

7.1: 91 percent / tetrahydrofuran / 16 h / Heating

8.1: 89 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / 0 °C

9.1: 73 percent / D-(-)-DET; Ti(OiPr)4; t-BuOOH / CH₂Cl₂; toluene / 2.75 h / -30 - -20 °C

10.1: 94 percent / tributylphosphine; triethylamine / 6 h / 0 - 20 °C

11.1: 56 percent / BF₃*OEt₂ / diethyl ether / 5 h / 0 - 20 °C

12.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 100 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

15.1: 532 mg / water; NaHCO₃ / acetonitrile / 16 h / 20 °C

16.1: t-BuLi / diethyl ether; pentane / 0.25 h / -100 - -90 °C

16.2: MgBr₂*OEt₂ / diethyl ether; pentane / 1 h / -90 - 0 °C

16.3: 85 percent / MgBr₂*OEt₂ / diethyl ether; pentane / -40 °C

17.1: 73 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 16 h / 0 °C

18.1: PPTS / CH₂Cl₂ / 0.08 h / 20 °C

18.2: BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / 20 °C

18.3: 99 percent / 2,6-lutidine

19.1: MeOH; K₂CO₃ / 17 h / 20 °C

20.1: 189 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

21.1: 92 percent / H₂ / Pd/C / ethyl acetate; propan-2-ol / 1 h / 20 °C / 760 Torr

22.1: 87 percent / triphenylphosphine; imidazole; iodine / toluene / 1 h / 20 °C

23.1: LDA / tetrahydrofuran / 0.5 h / -78 - 0 °C

23.2: 87 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 15 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; AD-mix-α; lithium aluminium tetrahydride; phosphate buffer; diethyl (2S,3S)-tartrate; tributylphosphine; methanesulfonamide; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; water; hydrogen; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; potassium osmate(VI); palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; diethylene glycol dimethyl ether; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; pentane; 3.1: Sharpless asymmetric dihydroxylation / 7.1: Wittig olefination / 9.1: Sharpless asymmetric epoxidation / 14.1: Pummerer rearrangement / 17.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo052073c

upstream raw materials:

(2R,3R,5S,2'S,5'S)-3-(tert-Butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-iodo-hexyl]-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

(E)-Henicos-3-en-1-ol

heneicos-3-yn-1-ol

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