(S)-6-Benzyloxy-1-{(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}-hexan-1-ol

Base Information

• Chemical Name: (S)-6-Benzyloxy-1-{(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}-hexan-1-ol
• CAS No.: 879290-56-9
• Molecular Formula: C₅₁H₉₆O₆Si₂
• Molecular Weight: 861.491
• Mol file: 879290-56-9.mol

Synonyms:(S)-6-Benzyloxy-1-{(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}-hexan-1-ol

Chemical Property of (S)-6-Benzyloxy-1-{(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}-hexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-Benzyloxy-1-{(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}-hexan-1-ol

There total 23 articles about (S)-6-Benzyloxy-1-{(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}-hexan-1-ol 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:

(E)-Henicos-3-en-1-ol (879290-72-9) → (S)-6-Benzyloxy-1-{(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}-hexan-1-ol (879290-56-9)

Guidance literature:

Multi-step reaction with 18 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

With 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; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; 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)-6-Benzyloxy-1-{(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}-hexan-1-ol (879290-56-9)

Guidance literature:

Multi-step reaction with 19 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

With 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; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; diethylene glycol dimethyl ether; 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

Reference yield:

1-[((E)-Henicos-3-enyl)oxymethyl]-4-methoxy-benzene (879290-36-5) → (S)-6-Benzyloxy-1-{(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}-hexan-1-ol (879290-56-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 92 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 20 h / 0 °C

2.1: 100 percent / triethylamine; DMAP / tetrahydrofuran / 3 h / 20 °C

3.1: 78 percent / DDQ; phosphate buffer / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

4.1: 96 percent / bisacetoxyiodobenzene; TEMPO / CH₂Cl₂ / 2 h / 20 °C

5.1: 91 percent / tetrahydrofuran / 16 h / Heating

6.1: 89 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / 0 °C

7.1: 73 percent / D-(-)-DET; Ti(OiPr)4; t-BuOOH / CH₂Cl₂; toluene / 2.75 h / -30 - -20 °C

8.1: 94 percent / tributylphosphine; triethylamine / 6 h / 0 - 20 °C

9.1: 56 percent / BF₃*OEt₂ / diethyl ether / 5 h / 0 - 20 °C

10.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 100 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

13.1: 532 mg / water; NaHCO₃ / acetonitrile / 16 h / 20 °C

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

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

14.3: 85 percent / MgBr₂*OEt₂ / diethyl ether; pentane / -40 °C

15.1: 73 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 16 h / 0 °C

16.1: PPTS / CH₂Cl₂ / 0.08 h / 20 °C

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

16.3: 99 percent / 2,6-lutidine

17.1: MeOH; K₂CO₃ / 17 h / 20 °C

With 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; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; pentane; 1.1: Sharpless asymmetric dihydroxylation / 5.1: Wittig olefination / 7.1: Sharpless asymmetric epoxidation / 12.1: Pummerer rearrangement / 15.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo052073c

upstream raw materials:

Acetic acid (S)-6-benzyloxy-1-{(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 ester

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

heneicos-3-yn-1-ol

1-[((E)-Henicos-3-enyl)oxymethyl]-4-methoxy-benzene

Downstream raw materials:

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

(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

C₃₉H₆₈O₆

C₅₁H₉₄O₆Si₂