(1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane

Base Information

• Chemical Name: (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane
• CAS No.: 259735-94-9
• Molecular Formula: C₂₁H₃₂O₄Se
• Molecular Weight: 427.443
• Mol file: 259735-94-9.mol

Synonyms:(1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property of (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane

There total 10 articles about (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane 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%

diphenyl diselenide (1666-13-3) + (1S,6R,8R,10S)-8-(3-Chloropropyl)-10-methoxy-3,3,9,9-tetramethyl-2,4,7-trioxabicyclo[4.4.0]decane (259735-93-8) → (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane (259735-94-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 0.666667h; Heating;

DOI:10.1055/s-1999-3633

Reference yield:

(R)-6-(3-Chloropropyl)-5,6-dihydro-5,5-dimethyl-4H-pyran-4-one (210691-79-5) → (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane (259735-94-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 24 h / 20 °C

1.2: 100 percent / CuBr*SMe₂; SMe₂ / tetrahydrofuran / 1 h / -70 - -30 °C

2.1: 87 percent / KF*2H₂O; H₂O₂; KHCO₃ / tetrahydrofuran; methanol; H₂O / 6 h / 0 °C

3.1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 36 h / 20 °C

4.1: 100 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 99 percent / 18-crown-6; oxone; KHCO₃ / acetone; H₂O; toluene / 1 h / 20 °C

6.1: 5 percent / PPTS; H₂O / methanol / 18 h / Heating

7.1: 86 percent / PPTS / CH₂Cl₂ / 4.25 h / 20 °C

8.1: 74 percent / CeCl₃*7H₂O; NaB(OAc)3H; H₂O / methanol / 4.25 h / 0 °C

9.1: 97 percent / Bu₄NHSO₄; NaOH / toluene; H₂O / 14 h / 20 °C

10.1: 100 percent / NaBH₄ / ethanol / 0.67 h / Heating

With dmap; Oxone; potassium fluoride; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; 18-crown-6 ether; water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; magnesium; ethylene dibromide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; 1.1: Grignard reaction / 1.2: Addition / 2.1: Oxidation / 3.1: Etherification / 4.1: Etherification / 5.1: Oxidation / 6.1: Hydrolysis / 7.1: Cycloaddition / 8.1: Reduction / 9.1: Etherification / 10.1: Substitution;

DOI:10.1055/s-1999-3633

Reference yield:

(2S,6R)-6-(3-Chloropropyl)-2-hydroxymethyl-5,5-dimethyltetrahydro-2H-pyran-4-one (259735-84-7) → (1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane (259735-94-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 36 h / 20 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

3: 99 percent / 18-crown-6; oxone; KHCO₃ / acetone; H₂O; toluene / 1 h / 20 °C

4: 5 percent / PPTS; H₂O / methanol / 18 h / Heating

5: 86 percent / PPTS / CH₂Cl₂ / 4.25 h / 20 °C

6: 74 percent / CeCl₃*7H₂O; NaB(OAc)3H; H₂O / methanol / 4.25 h / 0 °C

7: 97 percent / Bu₄NHSO₄; NaOH / toluene; H₂O / 14 h / 20 °C

8: 100 percent / NaBH₄ / ethanol / 0.67 h / Heating

With dmap; Oxone; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; 18-crown-6 ether; water; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; triethylamine; In methanol; ethanol; dichloromethane; water; acetone; toluene; 1: Etherification / 2: Etherification / 3: Oxidation / 4: Hydrolysis / 5: Cycloaddition / 6: Reduction / 7: Etherification / 8: Substitution;

DOI:10.1055/s-1999-3633

upstream raw materials:

diphenyl diselenide

(1S,6R,8R,10S)-8-(3-Chloropropyl)-10-methoxy-3,3,9,9-tetramethyl-2,4,7-trioxabicyclo[4.4.0]decane

(R)-6-(3-Chloropropyl)-5,6-dihydro-5,5-dimethyl-4H-pyran-4-one

(2S,6R)-6-(3-Chloropropyl)-2-hydroxymethyl-5,5-dimethyltetrahydro-2H-pyran-4-one