(1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one

Base Information

• Chemical Name: (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one
• CAS No.: 95682-14-7
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.505
• Mol file: 95682-14-7.mol

Synonyms:(1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one

Chemical Property of (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one

There total 3 articles about (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one 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: 93.0%

benzyl bromide (100-39-0) + (1R,4S,5S,6R,7R)-5-((R)-1-Hydroxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one (95682-28-3) → (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one (95682-14-7)

Guidance literature:

With potassium hydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(01)91292-4

Reference yield:

(1R,2S,3S,4S,5S)-1-Methoxymethoxy-3,5-dimethyl-8-oxo-bicyclo[2.2.2]octane-2-carbaldehyde (95682-27-2) → (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one (95682-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / ZnBr₂ / diethyl ether / -78 °C

2: 93 percent / KH / tetrahydrofuran / Ambient temperature

With potassium hydride; zinc dibromide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(01)91292-4

Reference yield:

(1S,2R,3S,4R,5R)-1-Methoxymethoxy-3,5-dimethyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester (95682-13-6) → (1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one (95682-14-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LiAlH₄; 2.) PCC, 4 Angstroem molecular sieves / 1.) Et₂O, RT; 2.) CH₂Cl₂

2: 95 percent / ZnBr₂ / diethyl ether / -78 °C

3: 93 percent / KH / tetrahydrofuran / Ambient temperature

With lithium aluminium tetrahydride; 4 A molecular sieve; potassium hydride; pyridinium chlorochromate; zinc dibromide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(01)91292-4

upstream raw materials:

benzyl bromide

(1R,4S,5S,6R,7R)-5-((R)-1-Hydroxy-but-3-enyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one

(1R,2S,3S,4S,5S)-1-Methoxymethoxy-3,5-dimethyl-8-oxo-bicyclo[2.2.2]octane-2-carbaldehyde

(1S,2R,3S,4R,5R)-1-Methoxymethoxy-3,5-dimethyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester

Downstream raw materials:

(1S,2R,4aR,6R,7R,8aR,9R)-2-Benzyloxy-4-hydroxymethyl-8a-methoxymethoxy-7,9-dimethyl-octahydro-1,6-methano-naphthalen-5-one

(1S,2R,4aR,6R,7R,8aR,9R)-2-Benzyloxy-8a-methoxymethoxy-7,9-dimethyl-4-methylene-octahydro-1,6-methano-naphthalen-5-one

(1R,4S,5S,6R,7R)-5-((R)-1-Benzyloxy-2-oxiranyl-ethyl)-4-methoxymethoxy-6,7-dimethyl-bicyclo[2.2.2]octan-2-one