(1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol

Base Information

• Chemical Name: (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol
• CAS No.: 1330616-23-3
• Molecular Formula: C₂₅H₃₃NO₂
• Molecular Weight: 379.543
• Mol file: 1330616-23-3.mol

Synonyms:(1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol

Chemical Property of (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol

There total 4 articles about (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol 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: 29.0%

(1S,2'R,4R,6R)-7,7-dimethylspiro[bicyclo[4.1.0]heptane-3,2'-oxiran]-4-ol (1330616-15-3) + (S)-N-benzyl-1-phenylethylamine (17480-69-2) → (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol (1330616-23-3)

Guidance literature:

With lithium perchlorate; In acetonitrile; for 40h; Reflux;

DOI:10.1016/j.tetasy.2011.06.013

Reference yield:

(+)-Δ3-carene (498-15-7,19079-29-9) → (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol (1330616-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1 h / 20 °C

2: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; diethylaluminium chloride / toluene / 2 h / 0 °C / Inert atmosphere

3: sodium phosphate dibasic dihydrate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

4: lithium perchlorate / acetonitrile / 40 h / Reflux

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; sodium phosphate dibasic dihydrate; lithium perchlorate; diethylaluminium chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; toluene; acetonitrile;

DOI:10.1016/j.tetasy.2011.06.013

Reference yield:

(-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol (4017-83-8,697298-84-3) → (1S,3R,4R,6R)-3-(benzyl((S)-1-phenylethyl)amino)methyl-7,7-dimethylbicyclo[4.1.0]heptane-3,4-diol (1330616-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium phosphate dibasic dihydrate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C

2: lithium perchlorate / acetonitrile / 40 h / Reflux

With sodium phosphate dibasic dihydrate; lithium perchlorate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2011.06.013

upstream raw materials:

(1S,2'R,4R,6R)-7,7-dimethylspiro[bicyclo[4.1.0]heptane-3,2'-oxiran]-4-ol

(S)-N-benzyl-1-phenylethylamine

(+)-Δ³-carene

(-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol