(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

Base Information

• Chemical Name: (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
• CAS No.: 879290-51-4
• Molecular Formula: C₅₇H₁₁₀O₆Si₃
• Molecular Weight: 975.753
• Mol file: 879290-51-4.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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) → (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 (879290-51-4)

Guidance literature:

Multi-step reaction with 19 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

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) → (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 (879290-51-4)

Guidance literature:

Multi-step reaction with 20 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

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) → (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 (879290-51-4)

Guidance literature:

Multi-step reaction with 18 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

18.1: 189 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °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:

(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

t-butyldimethylsiyl triflate

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

heneicos-3-yn-1-ol

Downstream raw materials:

(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