(2R,3R)-(+)-2,3-methanomethionine

Base Information

• Chemical Name: (2R,3R)-(+)-2,3-methanomethionine
• CAS No.: 143169-54-4
• Molecular Formula: C₆H₁₁NO₂S
• Molecular Weight: 161.225
• Mol file: 143169-54-4.mol

Synonyms:

Chemical Property of (2R,3R)-(+)-2,3-methanomethionine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-(+)-2,3-methanomethionine

There total 11 articles about (2R,3R)-(+)-2,3-methanomethionine 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: 52.0%

(1R,2R)-1--2-<(methylthio)methyl>cyclopropane-1-carbonitrile (143122-85-4) → (2R,3R)-(+)-2,3-methanomethionine (143169-54-4,143169-55-5)

Guidance literature:

With hydrogenchloride; for 19h; Heating;

DOI:10.1021/jo00048a028

Reference yield:

(1S,5R)-1-carboxy-2-oxo-3-oxabicyclo[3.1.0]hexane (143169-57-7) → (2R,3R)-(+)-2,3-methanomethionine (143169-54-4,143169-55-5)

Guidance literature:

Multi-step reaction with 10 steps

1: NEt₃, (PhO)2PON₃ / 17 h / Heating

2: 14.8M NH₄OH / 5 h / 25 °C

3: NEt₃, DMAP / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) 25 deg C, 3 h

4: 62 percent / TsCl, pyridine / 12 h / Heating

5: 35 h / 25 °C / Candida cylindracea, phosphate buffer pH 7.5

6: NEt₃ / CH₂Cl₂ / 0.5 h / 25 °C

7: Cs₂CO₃ / acetonitrile / 0.25 h / 65 °C

8: 89 percent / K₂CO₃ / methanol / 0.5 h / 0 °C

9: 50percent aq. NaOH / methanol / 0.5 h / 0 °C

10: 52 percent / 6M HCl / 19 h / Heating

With pyridine; hydrogenchloride; dmap; ammonium hydroxide; sodium hydroxide; diphenyl phosphoryl azide; potassium carbonate; caesium carbonate; triethylamine; p-toluenesulfonyl chloride; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00048a028

Reference yield:

(1R,5R)-(-)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane (143169-40-8) → (2R,3R)-(+)-2,3-methanomethionine (143169-54-4,143169-55-5)

Guidance literature:

Multi-step reaction with 11 steps

1: TFA / CH₂Cl₂ / 1.33 h / 25 °C

2: NEt₃, (PhO)2PON₃ / 17 h / Heating

3: 14.8M NH₄OH / 5 h / 25 °C

4: NEt₃, DMAP / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) 25 deg C, 3 h

5: 62 percent / TsCl, pyridine / 12 h / Heating

6: 35 h / 25 °C / Candida cylindracea, phosphate buffer pH 7.5

7: NEt₃ / CH₂Cl₂ / 0.5 h / 25 °C

8: Cs₂CO₃ / acetonitrile / 0.25 h / 65 °C

9: 89 percent / K₂CO₃ / methanol / 0.5 h / 0 °C

10: 50percent aq. NaOH / methanol / 0.5 h / 0 °C

11: 52 percent / 6M HCl / 19 h / Heating

With pyridine; hydrogenchloride; dmap; ammonium hydroxide; sodium hydroxide; diphenyl phosphoryl azide; potassium carbonate; caesium carbonate; triethylamine; p-toluenesulfonyl chloride; trifluoroacetic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00048a028

upstream raw materials:

(1R,2R)-1--2-<(methylthio)methyl>cyclopropane-1-carbonitrile

(1S,5R)-1-carboxy-2-oxo-3-oxabicyclo[3.1.0]hexane

(1R,5R)-(-)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane

(1R,2R)-(+)-1--2-(hydroxymethyl)cyclopropane-1-carbonitrile