3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester

Base Information

• Chemical Name: 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester
• CAS No.: 857685-63-3
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 857685-63-3.mol

Synonyms:3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester

Chemical Property of 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester

There total 8 articles about 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester 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%

(1R)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitrocyclopentane (857685-62-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester (857685-63-3)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In methanol; tert-butyl alcohol; at 20 ℃; for 48h;

DOI:10.1021/jo047882v

Reference yield:

methyl 2-(2-oxocyclopentyl)acetate (4934-95-6) → 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester (857685-63-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogen / [(R)-BINAP-RuCl₂](DMF)n / methanol / 24 h / 100 °C / 19001.3 Torr

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: tetrahydrofuran; hexane / 6 h / -78 °C

3.1: LiAlH₄ / tetrahydrofuran / 4 h / Heating

4.1: sodium hydride / tetrahydrofuran / 10 h / 20 °C

5.1: pyridinium chlorochromate; Celite / CH₂Cl₂ / 4 h / 20 °C

6.1: hydroxylamine hydrochloride; potassium carbonate / methanol / 4 h / 20 °C

7.1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

8.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

With disodium hydrogenphosphate; lithium aluminium tetrahydride; Celite; hydroxylamine hydrochloride; hydrogen; N-benzyl-trimethylammonium hydroxide; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; urea; pyridinium chlorochromate; lithium diisopropyl amide; [(R)-BINAP-RuCl₂](DMF)n; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; 8.1: Michael addition;

DOI:10.1016/j.tet.2007.03.031

Reference yield:

(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone oxime (857685-61-1) → 3-[1'-(S)-nitro-2'-(R)-(2''-benzyloxy-1''-(R)-methylethyl)-cyclopentyl]-propionic acid methyl ester (857685-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

2: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

With disodium hydrogenphosphate; N-benzyl-trimethylammonium hydroxide; 3-chloro-benzenecarboperoxoic acid; urea; In tetrahydrofuran; methanol; acetonitrile; tert-butyl alcohol; 2: Michael addition;

DOI:10.1016/j.tet.2007.03.031

upstream raw materials:

(1R)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitrocyclopentane

acrylic acid methyl ester

(3R,3aR,6aR)-3-methyl-hexahydrocyclopenta[b]furan-2-one

(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone

Downstream raw materials:

1-(R)-(2'-benzyloxy-1'-(R)-methyl-ethyl)-2-(S)-(3''-iodo-propyl)-2-(S)-nitro-cyclopentane

[(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde

1-(R)-(2'-benzyloxy-1'-(R)-methyl-ethyl)-7-(R)-[2''-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-aza-5-(S)-spiro[4.5]decane

(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane