(3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene

Base Information

• Chemical Name: (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene
• CAS No.: 479637-00-8
• Molecular Formula: C₃₅H₅₂O₄SeSi
• Molecular Weight: 643.841
• Mol file: 479637-00-8.mol

Synonyms:(3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene

Chemical Property of (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene

There total 14 articles about (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene 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: 98.0%

N-phenylselanylphthalimide (71098-88-9) + (1S,4aR,6S,8aR)-1-[2-hydroxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene (479636-99-2) → (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene (479637-00-8)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1016/S0040-4039(02)01859-2

Reference yield:

(4aS,6S,8aS)-6-hydroxy-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one (113666-05-0) → (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene (479637-00-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1.5 h / -78 °C

2.2: 74 percent / 2-phenylsulfonyl-3-phenyloxaziridine / tetrahydrofuran / 2 h / -78 °C

3.1: 98 percent / N,N-(diisopropyl)ethylamine / CH₂Cl₂ / 15 h / 20 °C

4.1: potassium tert-butoxide / benzene / 3 h / Heating

4.2: 91 percent / benzene / 16 h / Heating

5.1: 80 percent / lithium; NH₃ / tetrahydrofuran / 6 h / -78 - 20 °C

6.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: ethylene dibromide; magnesium / diethyl ether / 1 h / Heating

7.2: 95 percent / diethyl ether / 5 h / 20 °C

8.1: potassium tert-butoxide / benzene / 3 h / Heating

8.2: 97 percent / benzene / 13 h / Heating

9.1: 95 percent / lithium; NH₃ / tetrahydrofuran / 5 h / -78 - 20 °C

10.1: 98 percent / tin(IV) chloride / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; potassium tert-butylate; ammonia; sodium hexamethyldisilazane; tin(IV) chloride; lithium; Dess-Martin periodane; magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 4.2: Wittig reaction / 8.2: Wittig reaction;

DOI:10.1016/j.tet.2003.09.037

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4aR,6aS,12aR,12bS)-3-tert-butyldimethylsilyloxy-11-methoxymethoxy-4,4,12b-trimethyl-6a-phenylselenylmethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene (479637-00-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1.5 h / -78 °C

2.2: 74 percent / 2-phenylsulfonyl-3-phenyloxaziridine / tetrahydrofuran / 2 h / -78 °C

3.1: 98 percent / N,N-(diisopropyl)ethylamine / CH₂Cl₂ / 15 h / 20 °C

4.1: potassium tert-butoxide / benzene / 3 h / Heating

4.2: 91 percent / benzene / 16 h / Heating

5.1: 80 percent / lithium; NH₃ / tetrahydrofuran / 6 h / -78 - 20 °C

6.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: ethylene dibromide; magnesium / diethyl ether / 1 h / Heating

7.2: 95 percent / diethyl ether / 5 h / 20 °C

8.1: potassium tert-butoxide / benzene / 3 h / Heating

8.2: 97 percent / benzene / 13 h / Heating

9.1: 95 percent / lithium; NH₃ / tetrahydrofuran / 5 h / -78 - 20 °C

10.1: 98 percent / tin(IV) chloride / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; potassium tert-butylate; ammonia; sodium hexamethyldisilazane; tin(IV) chloride; lithium; Dess-Martin periodane; magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 4.2: Wittig reaction / 8.2: Wittig reaction;

DOI:10.1016/j.tet.2003.09.037

upstream raw materials:

N-phenylselanylphthalimide

(1S,4aR,6S,8aR)-1-[2-hydroxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene

(4aS,6S,8aS)-6-hydroxy-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one

t-butyldimethylsiyl triflate