7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester

Base Information

• Chemical Name: 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester
• CAS No.: 125180-08-7
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439
• Mol file: 125180-08-7.mol

Synonyms:7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester

Chemical Property of 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester

There total 7 articles about 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic 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: 93.0%

7-((1S,4R,5S,6R)-6-Hydroxymethyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester (125180-07-6) → 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester (125180-08-7)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃;

DOI:10.1021/ja00034a062

Reference yield:

(8R,9S)-8-Dimethylcarbamoyl-9-hydroxymethyl-undec-10-enoic acid methyl ester → 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester (125180-08-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / Ambient temperature

2: 1.) MeOTf, 2.) L-Selectride / 1,) CH₂Cl₂, RT, 2.) THF, -78 deg C

3: 5A molecular sieves

4: Heating

5: 82 percent / KOH / methanol

6: 93 percent / DMSO, (COCl)2 / CH₂Cl₂ / -60 °C

With potassium hydroxide; oxalyl dichloride; 5A molecular sieve; L-Selectride; dimethyl sulfoxide; triethylamine; methyl trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1021/ja00034a062

Reference yield:

(8R,9S)-9-Acetoxymethyl-8-formyl-undec-10-enoic acid methyl ester (125204-30-0,139528-66-8) → 7-((1S,4R,5S,6S)-6-Formyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester (125180-08-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 5A molecular sieves

2: Heating

3: 82 percent / KOH / methanol

4: 93 percent / DMSO, (COCl)2 / CH₂Cl₂ / -60 °C

With potassium hydroxide; oxalyl dichloride; 5A molecular sieve; dimethyl sulfoxide; In methanol; dichloromethane;

DOI:10.1021/ja00034a062

upstream raw materials:

7-((1S,4R,5S,6R)-6-Hydroxymethyl-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl)-heptanoic acid methyl ester

(8R,9S)-9-Acetoxymethyl-8-formyl-undec-10-enoic acid methyl ester

(8S,9R)-9-Acetoxymethyl-8-dimethylcarbamoyl-undec-10-enoic acid methyl ester

(8S,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-8-dimethylcarbamoyl-undec-10-enoic acid methyl ester

Downstream raw materials:

7-[(1R,4S,5R,6R)-6-((E)-3-Oxo-oct-1-enyl)-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl]-heptanoic acid methyl ester

7-[(1S,4R,5S,6S)-6-((E)-(S)-3-Hydroxy-oct-1-enyl)-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl]-heptanoic acid methyl ester

7-[(1S,4R,5S,6S)-6-((E)-(R)-3-Hydroxy-oct-1-enyl)-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl]-heptanoic acid methyl ester

7-[(1R,4S,5R,6R)-6-((E)-(S)-3-Hydroxy-oct-1-enyl)-3-phenyl-2-oxa-3-aza-bicyclo[2.2.1]hept-5-yl]-heptanoic acid methyl ester