phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate

Base Information

• Chemical Name: phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate
• CAS No.: 90719-46-3
• Molecular Formula: C₁₆H₁₈O₂
• Molecular Weight: 242.318
• Mol file: 90719-46-3.mol

Synonyms:phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate

Chemical Property of phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate

There total 12 articles about phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate 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: 95.0%

((1S,5R,7R)-10,10-Dimethyl-3-thioxo-4-oxa-2-aza-tricyclo[5.2.1.01,5]dec-2-yl)-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanone + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate (90719-46-3)

Guidance literature:

With dmap; In acetonitrile; at 25 ℃; for 72h;

DOI:10.1039/a900577c

Reference yield: 94.0%

(4S,1'R,2'R,3'S,4'S)-3-[(3'-methylbicyclo[2.2.1]hept-5'-ene-2'-yl)carbonyl]-4-iso-propyloxazolidin-2-one (90719-37-2) + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate (90719-46-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) -78 deg C; 2.) 0 deg C, 3 h;

DOI:10.1021/ja00212a037

Reference yield: 92.0%

(4S)-4-benzyl-3-(3-methylbicyclo[2.2.1]hept-5-ene-2-carbonyl)oxazolidin-2-one (90719-38-3) + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl (3R,4R,5S,6S)-5-methylbicyclo[2.2.1]heptene-4-carboxylate (90719-46-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) -78 deg C; 2.) 0 deg C, 3 h;

DOI:10.1021/ja00212a037

upstream raw materials:

lithium benzyloxide

(1S,2R,6S,7R,exo)-N-((3'R,4'S,5'S,6'R)-5'-methylbicyclo<2.2.1>heptene-4'-carbonyl)-3-oxa-5-aza-7,10,10-trimethyltricyclo<5.2.1.0^2,6>decan-4-one

(4S,1'R,2'R,3'S,4'S)-3-[(3'-methylbicyclo[2.2.1]hept-5'-ene-2'-yl)carbonyl]-4-iso-propyloxazolidin-2-one

benzyl alcohol