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

Base Information

• Chemical Name: 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
• CAS No.: 879290-50-3
• Molecular Formula: C₅₃H₉₈O₇Si₂
• Molecular Weight: 903.528
• Mol file: 879290-50-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 20 articles about 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 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) → 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 (879290-50-3)

Guidance literature:

Multi-step reaction with 17 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

With 2,6-dimethylpyridine; titanium(IV) isopropylate; 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; 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) → 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 (879290-50-3)

Guidance literature:

Multi-step reaction with 18 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

With 2,6-dimethylpyridine; titanium(IV) isopropylate; 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; 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) → 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 (879290-50-3)

Guidance literature:

Multi-step reaction with 16 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

With 2,6-dimethylpyridine; titanium(IV) isopropylate; 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; 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:

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

heneicos-3-yn-1-ol

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

tert-butyl-heneicos-3-ynyloxy-dimethyl-silane

Downstream 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

(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

C₄₇H₈₄O₇Si