(Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol

Base Information

• Chemical Name: (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol
• CAS No.: 879290-47-8
• Molecular Formula: C₅₁H₉₆O₅Si₂
• Molecular Weight: 845.491
• Mol file: 879290-47-8.mol

Synonyms:(Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol

Chemical Property of (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol

There total 26 articles about (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-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: 85.0%

((Z)-9-Iodo-non-6-enyloxymethyl)-benzene (879290-48-9) + (2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-carbaldehyde (879290-33-2) → (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol (879290-47-8)

Guidance literature:

((Z)-9-Iodo-non-6-enyloxymethyl)-benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -100 - -90 ℃; for 0.25h;

With magnesium bromide; In diethyl ether; pentane; at -90 - 0 ℃; for 1h;

(2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-carbaldehyde; With magnesium bromide; In diethyl ether; pentane; at -40 ℃;

DOI:10.1021/jo052073c

Reference yield:

(E)-Henicos-3-en-1-ol (879290-72-9) → (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol (879290-47-8)

Guidance literature:

Multi-step reaction with 15 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

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; 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;

DOI:10.1021/jo052073c

Reference yield:

heneicos-3-yn-1-ol (879290-35-4) → (Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol (879290-47-8)

Guidance literature:

Multi-step reaction with 16 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

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; 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;

DOI:10.1021/jo052073c

upstream raw materials:

((Z)-9-Iodo-non-6-enyloxymethyl)-benzene

(2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-carbaldehyde

(Z)-9-Benzyloxy-non-3-en-1-ol

(E)-Henicos-3-en-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

(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

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