3,4'-Dideoxy-5O-mycaminosyltylonolide

Base Information

• Chemical Name: 3,4'-Dideoxy-5O-mycaminosyltylonolide
• CAS No.: 127521-69-1
• Molecular Formula: C₃₁H₅₁NO₈
• Molecular Weight: 565.748
• ChEMBL ID: CHEMBL3634307
• Mol file: 127521-69-1.mol

Synonyms:3,4'-dideoxy-5O-mycaminosyltylonolide;3,4'-dideoxymycaminosyl tylonolide;3,4'-dideoxymycaminosyltylonolide;MC 352;MC-352

Chemical Property of 3,4'-Dideoxy-5O-mycaminosyltylonolide

Chemical Property:

• Vapor Pressure: 8.43E-25mmHg at 25°C
• Boiling Point: 733°C at 760 mmHg
• Flash Point: 397.1°C
• Density: 1.13g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 565.36146759
• Heavy Atom Count: 40
• Complexity: 887

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1C(C=C(C=CC(=O)C(CC(C(C(CCC(=O)O1)C)OC2C(C(CC(O2)C)N(C)C)O)CC=O)C)C)CO
• Isomeric SMILES: CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](CCC(=O)O1)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)CC=O)C)\C)CO

Technology Process of 3,4'-Dideoxy-5O-mycaminosyltylonolide

There total 15 articles about 3,4'-Dideoxy-5O-mycaminosyltylonolide 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:

5-O-mycaminosyltylonolide → 3-deoxy-5-O-(4-deoxymycaminosyl)tylonolide (127521-69-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / p-TsOH / benzene; acetonitrile / 2 h / Ambient temperature

2: 93 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

3: 84 percent / acetonitrile / Ambient temperature

4: 95 percent / pyridine / 3 h / Ambient temperature

5: 1.) 28percent aq. NH₃, 2.) MeOH / 1.) MeOH, RT, 3 h, 2.) 50 deg C, overnight

6: 55 percent / DIBAL / toluene / 0.5 h / -60 °C

7: pyridine / 3 h / -40 °C

8: NaI / butan-2-one / 0.5 h / 80 °C

9: 88 percent / Bu₃SnH, AIBN / benzene / 2 h / 80 °C

10: Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

11: 0.1 M aq. HCl / acetonitrile / 5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; methanol; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; benzene;

DOI:10.1246/bcsj.65.3405

Reference yield:

5-O-mycaminosyltylonolide 9,20-bis(ethylene acetal) → 3-deoxy-5-O-(4-deoxymycaminosyl)tylonolide (127521-69-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

2: 84 percent / acetonitrile / Ambient temperature

3: 95 percent / pyridine / 3 h / Ambient temperature

4: 1.) 28percent aq. NH₃, 2.) MeOH / 1.) MeOH, RT, 3 h, 2.) 50 deg C, overnight

5: 55 percent / DIBAL / toluene / 0.5 h / -60 °C

6: pyridine / 3 h / -40 °C

7: NaI / butan-2-one / 0.5 h / 80 °C

8: 88 percent / Bu₃SnH, AIBN / benzene / 2 h / 80 °C

9: Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

10: 0.1 M aq. HCl / acetonitrile / 5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; methanol; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; benzene;

DOI:10.1246/bcsj.65.3405

Reference yield:

23-O-(dimethylthexylsilyl)-5-O-mycaminosyltylonolide 9,20-bis(ethylene acetal) → 3-deoxy-5-O-(4-deoxymycaminosyl)tylonolide (127521-69-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / acetonitrile / Ambient temperature

2: 95 percent / pyridine / 3 h / Ambient temperature

3: 1.) 28percent aq. NH₃, 2.) MeOH / 1.) MeOH, RT, 3 h, 2.) 50 deg C, overnight

4: 55 percent / DIBAL / toluene / 0.5 h / -60 °C

5: pyridine / 3 h / -40 °C

6: NaI / butan-2-one / 0.5 h / 80 °C

7: 88 percent / Bu₃SnH, AIBN / benzene / 2 h / 80 °C

8: Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

9: 0.1 M aq. HCl / acetonitrile / 5 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium iodide; In tetrahydrofuran; toluene; acetonitrile; butanone; benzene;

DOI:10.1246/bcsj.65.3405

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