(1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate

Base Information

• Chemical Name: (1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate
• CAS No.: 127255-22-5
• Molecular Formula: C₁₇H₂₃NO₄Se
• Molecular Weight: 384.334
• Mol file: 127255-22-5.mol

Synonyms:(1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate

Chemical Property of (1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate

There total 7 articles about (1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate 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: 74.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + (1S,3S,4R)-methyl 3-(hydroxymethyl)-4,5,5-trimethylcyclopentanecarboxylate (127255-20-3) → (1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate (127255-22-5)

Guidance literature:

With tributylphosphine; In tetrahydrofuran;

DOI:10.1021/jo00300a021

Reference yield:

(1S,3R,5R)-3-(carbomethoxy)-4,4,5-trimethylcyclopentanecarboxylic acid (127308-34-3) → (1S,3R,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate (127255-22-5,127308-36-5)

Guidance literature:

Multi-step reaction with 2 steps

1: borane / tetrahydrofuran / 3 h

2: tri-n-butylphosphine / tetrahydrofuran

With tributylphosphine; borane; In tetrahydrofuran;

DOI:10.1021/jo00300a021

Reference yield:

methyl phenylcamphorate (127308-32-1) → (1S,3S,4R)-methyl 3-<<(o-nitrophenyl)seleno>methyl>-4,5,5-trimethylcyclopentanecarboxylate (127255-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / NaIO₄, RuO₄ / CCl₄; acetonitrile; H₂O / 72 h

2: 93 percent / borane / tetrahydrofuran / 3 h / 0 °C

3: 74 percent / tri-n-butylphosphine / tetrahydrofuran

With sodium periodate; ruthenium tetroxide; tributylphosphine; borane; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1021/jo00300a021

upstream raw materials:

ortho-nitrophenyl selenocyanate

(1S,3S,4R)-methyl 3-(hydroxymethyl)-4,5,5-trimethylcyclopentanecarboxylate

(1S,3S,5R)-3-(carbomethoxy)-4,4,5-trimethylcyclopentanecarboxylic acid

methyl phenylcamphorate

Downstream raw materials:

(-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanemethanol