[(3S,6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate

Base Information

• Chemical Name: [(3S,6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate
• CAS No.: 167173-85-5
• Molecular Formula: C26H30 N2 O9
• Molecular Weight: 514.532
• European Community (EC) Number: 844-009-5
• DSSTox Substance ID: DTXSID501101266
• Nikkaji Number: J959.715H
• Wikidata: Q105166602
• Metabolomics Workbench ID: 125587
• ChEMBL ID: CHEMBL193357
• Mol file: 167173-85-5.mol

Synonyms:fenpicoxamid;UK 2A;UK-2A

Chemical Property of [(3S,6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate

Chemical Property:

• PSA: 150.35000
• LogP: 2.20030
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 514.19513054
• Heavy Atom Count: 37
• Complexity: 814

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(=O)OCC(C(=O)O1)NC(=O)C2=NC=CC(=C2O)OC)CC3=CC=CC=C3)OC(=O)C(C)C
• Isomeric SMILES: C[C@H]1[C@@H]([C@H](C(=O)OC[C@@H](C(=O)O1)NC(=O)C2=NC=CC(=C2O)OC)CC3=CC=CC=C3)OC(=O)C(C)C

Technology Process of [(3S,6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate

There total 15 articles about [(3S,6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate 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:

3-hydroxy-4-methoxy-pyridine-2-carboxylic acid (210300-09-7) + isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester (210300-07-5) → (3S,6S,7R,8R)-8-benzyl-3-{[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate (167173-85-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 25 ℃; Yield given;

DOI:10.1016/S0040-4039(98)00796-5

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (3S,6S,7R,8R)-8-benzyl-3-{[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate (167173-85-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 78 percent / n-butyllithium / tetrahydrofuran / 3 h / -78 °C

3: aq. H₂O₂, LiOH / 12 h / 25 °C

4: 89 percent / triphenylphosphine, DIAD / tetrahydrofuran / 0.67 h / 25 °C

5: 99 percent / imidazole / dimethylformamide / 17 h / 60 °C

6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.5 h / 25 °C

7: DMAP, EDCI / CH₂Cl₂ / 2 h / 10 °C

8: 100 percent / H₂ / Pd(OH)2 / ethanol / 14 h / 25 °C / 3040 Torr

9: 87 percent / Ph₃P, DIAD / CH₂Cl₂ / 24 h / 25 °C

10: 100 percent / HF, pyridine / tetrahydrofuran / 72 h / Ambient temperature

11: 94 percent / pyridine / 5.5 h / 0 °C

12: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

13: HOBt, EDCI*HCl, N-methylmorpholine / dimethylformamide / 10 h / 25 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; dmap; lithium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00777-7

Reference yield:

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one (96837-44-4) → (3S,6S,7R,8R)-8-benzyl-3-{[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate (167173-85-5)

Guidance literature:

Multi-step reaction with 12 steps

2: aq. H₂O₂, LiOH / 12 h / 25 °C

3: 89 percent / triphenylphosphine, DIAD / tetrahydrofuran / 0.67 h / 25 °C

4: 99 percent / imidazole / dimethylformamide / 17 h / 60 °C

5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.5 h / 25 °C

6: DMAP, EDCI / CH₂Cl₂ / 2 h / 10 °C

7: 100 percent / H₂ / Pd(OH)2 / ethanol / 14 h / 25 °C / 3040 Torr

8: 87 percent / Ph₃P, DIAD / CH₂Cl₂ / 24 h / 25 °C

9: 100 percent / HF, pyridine / tetrahydrofuran / 72 h / Ambient temperature

10: 94 percent / pyridine / 5.5 h / 0 °C

11: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

12: HOBt, EDCI*HCl, N-methylmorpholine / dimethylformamide / 10 h / 25 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; dmap; lithium hydroxide; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00777-7

upstream raw materials:

3-hydroxy-4-methoxy-pyridine-2-carboxylic acid

isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one

hydrocinnamic acid chloride

Downstream raw materials:

(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one

methyl-(3,4-dimethoxypicolinyl)serine

[(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]-2-methylpropanoate

Heptanedioic acid benzyl ester 2-((3S,7R,8R,9S)-7-benzyl-8-isobutyryloxy-9-methyl-2,6-dioxo-[1,5]dioxonan-3-ylcarbamoyl)-4-methoxy-pyridin-3-yl ester