(2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane

Base Information

• Chemical Name: (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane
• CAS No.: 879290-34-3
• Molecular Formula: C₄₁H₇₈O₃SSi₂
• Molecular Weight: 707.306
• Mol file: 879290-34-3.mol

Synonyms:(2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane

Chemical Property of (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane

There total 11 articles about (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane 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: 94.0%

[(2R,3R)-3-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-oxiranyl]-methanol (879290-40-1) + diphenyldisulfane (882-33-7) → (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane (879290-34-3)

Guidance literature:

With tributylphosphine; triethylamine; at 0 - 20 ℃; for 6h;

DOI:10.1021/jo052073c

Reference yield:

(E)-Henicos-3-en-1-ol (879290-72-9) → (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane (879290-34-3)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

4: 78 percent / DDQ; phosphate buffer / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

5: 96 percent / bisacetoxyiodobenzene; TEMPO / CH₂Cl₂ / 2 h / 20 °C

6: 91 percent / tetrahydrofuran / 16 h / Heating

7: 89 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / 0 °C

8: 73 percent / D-(-)-DET; Ti(OiPr)4; t-BuOOH / CH₂Cl₂; toluene / 2.75 h / -30 - -20 °C

9: 94 percent / tributylphosphine; triethylamine / 6 h / 0 - 20 °C

With 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; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; toluene; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation / 6: Wittig olefination / 8: Sharpless asymmetric epoxidation;

DOI:10.1021/jo052073c

Reference yield:

heneicos-3-yn-1-ol (879290-35-4) → (2R,3S)-2-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-3-phenylsulfanylmethyl-oxirane (879290-34-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / LAH / bis-(2-methoxy-ethyl) ether / 17 h / 125 °C

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

3: 92 percent / AD-mix-α; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 20 h / 0 °C

4: 100 percent / triethylamine; DMAP / tetrahydrofuran / 3 h / 20 °C

5: 78 percent / DDQ; phosphate buffer / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

6: 96 percent / bisacetoxyiodobenzene; TEMPO / CH₂Cl₂ / 2 h / 20 °C

7: 91 percent / tetrahydrofuran / 16 h / Heating

8: 89 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / 0 °C

9: 73 percent / D-(-)-DET; Ti(OiPr)4; t-BuOOH / CH₂Cl₂; toluene / 2.75 h / -30 - -20 °C

10: 94 percent / tributylphosphine; triethylamine / 6 h / 0 - 20 °C

With 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; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; diethylene glycol dimethyl ether; toluene; tert-butyl alcohol; 3: Sharpless asymmetric dihydroxylation / 7: Wittig olefination / 9: Sharpless asymmetric epoxidation;

DOI:10.1021/jo052073c

upstream raw materials:

[(2R,3R)-3-((2S,3S)-2,3-Bis-triethylsilanyloxy-icosyl)-oxiranyl]-methanol

diphenyldisulfane

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

heneicos-3-yn-1-ol

Downstream raw materials:

(2S,3R,5S)-5-((S)-1-Hydroxy-octadecyl)-2-phenylsulfanylmethyl-tetrahydro-furan-3-ol

(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