DIMETHYL (1S,9S)-5-CYANOSEMICORRIN-1,9-DICARBOXYLATE

Base Information

• Chemical Name: DIMETHYL (1S,9S)-5-CYANOSEMICORRIN-1,9-DICARBOXYLATE
• CAS No.: 105251-49-8
• Molecular Formula: C₁₄H₁₇N₃O₄
• Molecular Weight: 291.307
• Mol file: 105251-49-8.mol

Synonyms:2H-Pyrrole-2-carboxylicacid, 5-[cyano[5-(methoxycarbonyl)-2-pyrrolidinylidene]methyl]-3,4-dihydro-,methyl ester, [2S-[2R*,5[E(R*)]]]-; (1S,9S)-Dimethyl5-cyanosemicorrin-1,9-dicarboxylate

Chemical Property of DIMETHYL (1S,9S)-5-CYANOSEMICORRIN-1,9-DICARBOXYLATE

Chemical Property:

• Vapor Pressure: 5.88E-07mmHg at 25°C
• Melting Point: 77-79 °C(lit.)
• Refractive Index: 1.612
• Boiling Point: 410.8°Cat760mmHg
• Flash Point: 202.2°C
• PSA: 100.78000
• Density: 1.36g/cm³
• LogP: 0.22988

Purity/Quality:

99% ^*data from raw suppliers

DIMETHYL (1S,9S)-5-CYANOSEMICORRIN-1,9-DICARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DIMETHYL (1S,9S)-5-CYANOSEMICORRIN-1,9-DICARBOXYLATE

There total 6 articles about DIMETHYL (1S,9S)-5-CYANOSEMICORRIN-1,9-DICARBOXYLATE 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: 75.0%

(2S)-methyl 5-(cyanomethylidene)pyrrolidine-2-carboxylate (65571-72-4,65571-73-5,65571-74-6,65571-75-7) + (2S)-methyl 5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylate (65571-69-9) → (1S,9S)-dimethyl 5-cyanosemicorrin-1,9-dicarboxylate (105251-49-8)

Guidance literature:

With trifluoroacetic acid; In 1,2-dichloro-ethane; at 65 ℃; for 4.5h;

DOI:10.1002/hlca.19880710620

Reference yield:

methyl (S)-pyroglutamate (4931-66-2) → (1S,9S)-dimethyl 5-cyanosemicorrin-1,9-dicarboxylate (105251-49-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / CH₂Cl₂ / 5 h / Heating

2: 81 percent / 23 h / 100 °C

3: CF₃CO₂H / 0.13 h / 23 °C

4: 75 percent / CF₃CO₂H / 1,2-dichloro-ethane / 4.5 h / 65 °C

With trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19880710620

Reference yield:

(2S)-methyl 5-<<(tert-butyl)oxycarbonyl>(cyano)methylidene>pyrrolidine-2-carboxylate (105367-32-6) → (1S,9S)-dimethyl 5-cyanosemicorrin-1,9-dicarboxylate (105251-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃CO₂H / 0.13 h / 23 °C

2: 75 percent / CF₃CO₂H / 1,2-dichloro-ethane / 4.5 h / 65 °C

With trifluoroacetic acid; In 1,2-dichloro-ethane;

DOI:10.1002/hlca.19880710620

upstream raw materials:

(2S)-methyl 5-(cyanomethylidene)pyrrolidine-2-carboxylate

(2S)-methyl 5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylate

(2S)-methyl 5-<<(tert-butyl)oxycarbonyl>(cyano)methylidene>pyrrolidine-2-carboxylate

methyl (S)-pyroglutamate

Downstream raw materials:

(1S,9S)-1,9-bis<<(tert-butyl)dimethylsilyl>methyl>semicorrin-5-carbonitrile

(1S,9S)-1,9-bis(1-hydroxy-1-methylethyl)semicorrin-5-carbonitrile