Unii-MP4G742tkl

Base Information

• Chemical Name: Unii-MP4G742tkl
• CAS No.: 144574-07-2
• Molecular Formula: C₁₅H₂₁N₃O₄
• Molecular Weight: 307.349
• UNII: MP4G742TKL
• Nikkaji Number: J907.606I
• Mol file: 144574-07-2.mol

Synonyms:GV 129606;GV-129606;GV129606

Chemical Property of Unii-MP4G742tkl

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 307.15320616
• Heavy Atom Count: 22
• Complexity: 573

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1C2C3CCCC(C3=C(N2C1=O)C(=O)O)N(C)C=N)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@H]2[C@H]3CCC[C@@H](C3=C(N2C1=O)C(=O)O)N(C)C=N)O

Technology Process of Unii-MP4G742tkl

There total 9 articles about Unii-MP4G742tkl 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: 42.0%

methanimidic acid phenylmethyl ester hydrochloride (60099-09-4) + (1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methylamino-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid (144574-08-3) → GV129606 (144574-07-2)

Guidance literature:

With IRA₆₈ resin; In water; acetonitrile; at 0 ℃;

DOI:10.1016/S0040-4020(00)00414-2

Reference yield:

(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (135297-04-0) → GV129606 (144574-07-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 78 percent / LiClO₄ / acetonitrile / 3.5 h / 60 °C

2: 86 percent / diisopropylamine / CH₂Cl₂ / 2 h / 0 °C

3: 79 percent / oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -70 °C

4: 94.6 percent / potassium carbonate; pyridine / CH₂Cl₂ / 0 - 25 °C

5: 88.5 percent / P(OEt)3 / various solvent(s) / 5 h / Heating

6: 61 percent / tetrabutylammonium bromide; aq. AcOH; cesium fluoride / tetrahydrofuran / 4 h / 40 °C

7: 60 percent / H₂ / 20 percent Pd/C / H₂O; propan-2-ol / 2.5 h / 760 Torr

8: 42 percent / IRA₆₈ resin / H₂O; acetonitrile / 0 °C

With pyridine; oxalyl dichloride; IRA₆₈ resin; tetrabutylammomium bromide; hydrogen; lithium perchlorate; potassium carbonate; acetic acid; dimethyl sulfoxide; diisopropylamine; cesium fluoride; triethyl phosphite; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; acetonitrile; 1: Substitution / 2: Acylation / 3: Oxidation / 4: Acylation / 5: Cyclization / 6: desilylation / 7: Hydrogenolysis / 8: Substitution;

DOI:10.1016/S0040-4020(00)00414-2

Reference yield:

(3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one (135297-03-9) → GV129606 (144574-07-2)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. magnesium monoperoxyphthalate / CH₂Cl₂ / 24 h

2: 78 percent / LiClO₄ / acetonitrile / 3.5 h / 60 °C

3: 86 percent / diisopropylamine / CH₂Cl₂ / 2 h / 0 °C

4: 79 percent / oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -70 °C

5: 94.6 percent / potassium carbonate; pyridine / CH₂Cl₂ / 0 - 25 °C

6: 88.5 percent / P(OEt)3 / various solvent(s) / 5 h / Heating

7: 61 percent / tetrabutylammonium bromide; aq. AcOH; cesium fluoride / tetrahydrofuran / 4 h / 40 °C

8: 60 percent / H₂ / 20 percent Pd/C / H₂O; propan-2-ol / 2.5 h / 760 Torr

9: 42 percent / IRA₆₈ resin / H₂O; acetonitrile / 0 °C

With pyridine; oxalyl dichloride; IRA₆₈ resin; tetrabutylammomium bromide; hydrogen; lithium perchlorate; potassium carbonate; magnesium monoperoxyphthalate hexahydrate; acetic acid; dimethyl sulfoxide; diisopropylamine; cesium fluoride; triethyl phosphite; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; acetonitrile; 1: Epoxidation / 2: Substitution / 3: Acylation / 4: Oxidation / 5: Acylation / 6: Cyclization / 7: desilylation / 8: Hydrogenolysis / 9: Substitution;

DOI:10.1016/S0040-4020(00)00414-2

upstream raw materials:

methanimidic acid phenylmethyl ester hydrochloride

(1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methylamino-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid

(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

(3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one