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

Base Information

• Chemical Name: (1S,4aR,6S,8aR)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene
• CAS No.: 479636-98-1
• Molecular Formula: C₃₇H₅₆O₅Si
• Molecular Weight: 608.934
• Mol file: 479636-98-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (1S,4aR,6S,8aR)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene 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: 97.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1R,4aR,6S,8aS)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-one (479636-97-0) → (1S,4aR,6S,8aR)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene (479636-98-1)

Guidance literature:

With potassium tert-butylate; In benzene; Heating;

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

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1S,4aR,6S,8aR)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene (479636-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / N,N-(diisopropyl)ethylamine / CH₂Cl₂ / 1 h / 20 °C

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

2.2: 95 percent / diethyl ether / 5 h / 20 °C

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

3.2: 97 percent / benzene / 13 h / Heating

With potassium tert-butylate; magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; benzene; 3.2: Wittig reaction;

DOI:10.1016/j.tet.2003.09.037

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (1S,4aR,6S,8aR)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-2-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene (479636-98-1)

Guidance literature:

Multi-step reaction with 8 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

With 2,6-dimethylpyridine; potassium tert-butylate; ammonia; sodium hexamethyldisilazane; 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:

Methyltriphenylphosphonium bromide

(1R,4aR,6S,8aS)-1-[2-benzyloxymethoxy-6-(methoxymethoxy)benzyl]-6-tert-butyldimethylsiloxy-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Benzyloxymethyl chloride

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

Downstream raw materials:

(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

(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