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

Base Information

• Chemical Name: (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan
• CAS No.: 1054618-90-4
• Molecular Formula: C₄₁H₇₈O₄SSi₂
• Molecular Weight: 723.305
• Mol file: 1054618-90-4.mol

Synonyms:(2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan

Chemical Property of (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan

There total 16 articles about (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan 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: 100.0%

(2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-2-phenylsulfanylmethyl-tetrahydro-furan (879290-42-3) → (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan (1054618-90-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo052073c

Reference yield:

(E)-Henicos-3-en-1-ol (879290-72-9) → (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan (1054618-90-4)

Guidance literature:

Multi-step reaction with 12 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

10: 56 percent / BF₃*OEt₂ / diethyl ether / 5 h / 0 - 20 °C

11: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

12: 100 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °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; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 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) → (2S,3R,5S)-2-Benzenesulfinylmethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan (1054618-90-4)

Guidance literature:

Multi-step reaction with 13 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

11: 56 percent / BF₃*OEt₂ / diethyl ether / 5 h / 0 - 20 °C

12: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

13: 100 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °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; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 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; tert-butyl alcohol; 3: Sharpless asymmetric dihydroxylation / 7: Wittig olefination / 9: Sharpless asymmetric epoxidation;

DOI:10.1021/jo052073c

upstream raw materials:

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

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

heneicos-3-yn-1-ol

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

Downstream raw materials:

(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

(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

(R)-6-Benzyloxy-1-{(2S,5R,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

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