(3Z,5S,6S,7S,9R,11Z,13Z,15S,16R)-16-ethyl-6-hydroxy-5,7,9,15-tetramethyl-1-oxacyclohexadeca-3,11,13-triene-2,10-dione

Base Information

• Chemical Name: (3Z,5S,6S,7S,9R,11Z,13Z,15S,16R)-16-ethyl-6-hydroxy-5,7,9,15-tetramethyl-1-oxacyclohexadeca-3,11,13-triene-2,10-dione
• CAS No.: 79495-87-7
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483
• Mol file: 79495-87-7.mol

Synonyms:protomycinolide IV

Chemical Property of (3Z,5S,6S,7S,9R,11Z,13Z,15S,16R)-16-ethyl-6-hydroxy-5,7,9,15-tetramethyl-1-oxacyclohexadeca-3,11,13-triene-2,10-dione

Chemical Property:

• Vapor Pressure: 3.15E-13mmHg at 25°C
• Melting Point: 158.5 - 160 °C
• Boiling Point: 525.3°C at 760 mmHg
• Flash Point: 177.9°C
• PSA: 63.60000
• Density: 0.961g/cm³
• LogP: 3.85490
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 348.23005950
• Heavy Atom Count: 25
• Complexity: 532

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1C(C=CC=CC(=O)C(CC(C(C(C=CC(=O)O1)C)O)C)C)C
• Isomeric SMILES: CC[C@@H]1[C@H](/C=C\C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](/C=C\C(=O)O1)C)O)C)C)C

Technology Process of (3Z,5S,6S,7S,9R,11Z,13Z,15S,16R)-16-ethyl-6-hydroxy-5,7,9,15-tetramethyl-1-oxacyclohexadeca-3,11,13-triene-2,10-dione

There total 69 articles about (3Z,5S,6S,7S,9R,11Z,13Z,15S,16R)-16-ethyl-6-hydroxy-5,7,9,15-tetramethyl-1-oxacyclohexadeca-3,11,13-triene-2,10-dione 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: 68.0%

(4S,5S,6S,8R,9RS,14S,15R)-(2E,10E,12E)-5,9-dihydroxy-4,6,8,14-tetramethyl-2,10,12-heptadecatrien-15-olide → protomycinolide IV (79495-87-7)

Guidance literature:

With manganese(IV) oxide; In diethyl ether; for 2.5h; Ambient temperature;

DOI:10.1021/ja00277a028

Reference yield:

(R)-(Z)-5-<(benzyloxy)methoxy>-2-methyl-3-(trimethylsilyl)-3-penten-1-ol (103563-35-5) → protomycinolide IV (79495-87-7)

Guidance literature:

Multi-step reaction with 22 steps

1: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

2: CrCl₂ / tetrahydrofuran / 0 °C

3: 94 percent / PPTS / CH₂Cl₂ / Ambient temperature

4: 1.) dicyclohexyl borane, 2.) H₂O₂ / 1.) THF, 0 deg C

5: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

6: HCl / dioxane / Ambient temperature

7: KH / 1,2-dimethoxy-ethane / 0.5 h / Ambient temperature

8: 0.02N HCl / dioxane / 1 h / Ambient temperature

9: 92 percent / HgCl₂ / acetonitrile; tetrahydrofuran / 1 h / Ambient temperature; pH 7 phosphate buffer

10: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

11: 97 percent / PhSH, BF₃*Et₂O / CH₂Cl₂ / 12 h / 0 °C

12: 95 percent / PPTS / Ambient temperature

13: 91 percent / n-BuLi / hexane / 0.5 h / 0 °C

14: 65 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

15: 98 percent / pyridine / Ambient temperature

16: 99 percent / PPTS / methanol / Ambient temperature

17: MnO₂ / diethyl ether / 2.5 h / Ambient temperature

18: NaClO₂, resorcinol / 2-methyl-propan-2-ol; H₂O / Ambient temperature; pH 4 acetate buffer

19: Et₃N / tetrahydrofuran / 3 h / Ambient temperature

20: 4-pyrrolidinopyridine / toluene / 14 h / Heating

21: 1N aq. LiOH / methanol / 6 h / 30 °C

22: 68 percent / MnO₂ / diethyl ether / 2.5 h / Ambient temperature

With pyridine; chromium dichloride; hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium chlorite; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; thiophenol; triethylamine; mercury dichloride; lithium diisopropyl amide; recorcinol; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00277a028

Reference yield:

(R)-(Z)-5-<(benzyloxy)methoxy>-2-methyl-3-(trimethylsilyl)-3-pentenal (103563-36-6) → protomycinolide IV (79495-87-7)

Guidance literature:

Multi-step reaction with 21 steps

1: CrCl₂ / tetrahydrofuran / 0 °C

2: 94 percent / PPTS / CH₂Cl₂ / Ambient temperature

3: 1.) dicyclohexyl borane, 2.) H₂O₂ / 1.) THF, 0 deg C

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

5: HCl / dioxane / Ambient temperature

6: KH / 1,2-dimethoxy-ethane / 0.5 h / Ambient temperature

7: 0.02N HCl / dioxane / 1 h / Ambient temperature

8: 92 percent / HgCl₂ / acetonitrile; tetrahydrofuran / 1 h / Ambient temperature; pH 7 phosphate buffer

9: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

10: 97 percent / PhSH, BF₃*Et₂O / CH₂Cl₂ / 12 h / 0 °C

11: 95 percent / PPTS / Ambient temperature

12: 91 percent / n-BuLi / hexane / 0.5 h / 0 °C

13: 65 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

14: 98 percent / pyridine / Ambient temperature

15: 99 percent / PPTS / methanol / Ambient temperature

16: MnO₂ / diethyl ether / 2.5 h / Ambient temperature

17: NaClO₂, resorcinol / 2-methyl-propan-2-ol; H₂O / Ambient temperature; pH 4 acetate buffer

18: Et₃N / tetrahydrofuran / 3 h / Ambient temperature

19: 4-pyrrolidinopyridine / toluene / 14 h / Heating

20: 1N aq. LiOH / methanol / 6 h / 30 °C

21: 68 percent / MnO₂ / diethyl ether / 2.5 h / Ambient temperature

With pyridine; chromium dichloride; hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium chlorite; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; thiophenol; triethylamine; mercury dichloride; lithium diisopropyl amide; recorcinol; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00277a028

upstream raw materials:

(3E,11E,13E)-(5S,6S,7S,9R,15S,16R)-6-(tert-Butyl-dimethyl-silanyloxy)-16-ethyl-5,7,9,15-tetramethyl-oxacyclohexadeca-3,11,13-triene-2,10-dione

(E)-(2R,4S,5S,6S)-5,9-dihydroxy-2,4,6-trimethyl-7-nonenecarboxylic Acid γ-Lactone

(3R,4S)-(E)-7-<(benzyloxy)methoxy>-4-methyl-5-hepten-3-ol

(R)-(Z)-5-<(benzyloxy)methoxy>-2-methyl-3-(trimethylsilyl)-3-penten-1-ol

Downstream raw materials:

Myconolide IV

Refernces

• 1、 Honda, Masanori,Katsuki, Tsutomu,Yamaguchi, Masaru. "TOTAL SYNTHESIS OF PROTOMYCINOLIDE IV". . p. 3857 - 3860. Retrieved 2007/10/02.