(1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

Base Information

• Chemical Name: (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester
• CAS No.: 135613-49-9
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 135613-49-9.mol

Synonyms:(1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

Chemical Property of (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

There total 12 articles about (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]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: 80.0%

<1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid, methyl ester (135682-53-0) → (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester (135613-49-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1021/jm00113a030

Reference yield: 72.1%

<1S-(1α,2α,3α,4α)>-2-<(3-carboxy-7-oxabicyclo<2.2.1>hept-2-yl)methyl>benzenepropanoic acid methyl ester (142757-91-3) → (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester (135613-49-9)

Guidance literature:

<1S-(1α,2α,3α,4α)>-2-<(3-carboxy-7-oxabicyclo<2.2.1>hept-2-yl)methyl>benzenepropanoic acid methyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 2h;

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1002/jccs.200100132

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → (1R,2S,3R,4S)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester (135613-49-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / tetrahydrofuran / 18 h / 25 °C

2: 97 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 3 h

3: 100 percent / diisobutylaluminum hydride / toluene / 1.) -78 deg C, 2 h, 2.) from -78 deg C to 0 deg C, 2 h

4: 92 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 4 h / 25 °C

5: 1.) tert-butyllithium / 1.) ether, pentane, a) -100 deg C, 15 min, b) 0 deg C, 15 min, 2.) ether, pentane, THF, 0 deg C, 1 h

6: 55 percent / H₂, glacial HOAc / 20percent Pd(OH)2/C / 5 h / 760 Torr

7: 4-(dimethylamino)pyridine, pyridine / 2 h / 25 °C

8: CrO₃, H₂SO₄ / acetone / 2 h / 0 °C

9: 1 M aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C

10: HCl / 2 h / 0 °C

11: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 25 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; sodium hydroxide; sulfuric acid; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; palladium dihydroxide; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1021/jm00113a030

upstream raw materials:

<1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid, methyl ester

<1S-(1α,2α,3α,4α)>-2-<(3-carboxy-7-oxabicyclo<2.2.1>hept-2-yl)methyl>benzenepropanoic acid methyl ester

ortho-bromobenzaldehyde

3-(2-bromophenyl)propanoic acid,methyl ester

Downstream raw materials:

3-[2-((1S,2R,3R,4R)-3-Isocyanato-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-propionic acid methyl ester

(1R,2R,3R,4S)-3-[2-(3-carboxy-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

anti-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid

syn-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid