(7Z,11Z)-4,10,13,18-tetrahydroxy-1,3,7,11,20a-pentamethyl-20,21-dioxo-1,2,3,4,4a,6a,9,10,12a,13,16,20,20a,20b-tetradecahydro-16a,19-methanobenzo[b]naphtho[2,1-j]oxacyclotetradecine-15-carbaldehyde

Base Information

• Chemical Name: (7Z,11Z)-4,10,13,18-tetrahydroxy-1,3,7,11,20a-pentamethyl-20,21-dioxo-1,2,3,4,4a,6a,9,10,12a,13,16,20,20a,20b-tetradecahydro-16a,19-methanobenzo[b]naphtho[2,1-j]oxacyclotetradecine-15-carbaldehyde
• CAS No.: 76705-48-1
• Molecular Formula: C₃₂H₄₀O₈
• Molecular Weight: 552.665
• Mol file: 76705-48-1.mol

Synonyms:

Chemical Property of (7Z,11Z)-4,10,13,18-tetrahydroxy-1,3,7,11,20a-pentamethyl-20,21-dioxo-1,2,3,4,4a,6a,9,10,12a,13,16,20,20a,20b-tetradecahydro-16a,19-methanobenzo[b]naphtho[2,1-j]oxacyclotetradecine-15-carbaldehyde

Chemical Property:

• Vapor Pressure: 8.1E-27mmHg at 25°C
• Boiling Point: 762.2°Cat760mmHg
• Flash Point: 245.2°C
• Density: 1.33g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (7Z,11Z)-4,10,13,18-tetrahydroxy-1,3,7,11,20a-pentamethyl-20,21-dioxo-1,2,3,4,4a,6a,9,10,12a,13,16,20,20a,20b-tetradecahydro-16a,19-methanobenzo[b]naphtho[2,1-j]oxacyclotetradecine-15-carbaldehyde

There total 41 articles about (7Z,11Z)-4,10,13,18-tetrahydroxy-1,3,7,11,20a-pentamethyl-20,21-dioxo-1,2,3,4,4a,6a,9,10,12a,13,16,20,20a,20b-tetradecahydro-16a,19-methanobenzo[b]naphtho[2,1-j]oxacyclotetradecine-15-carbaldehyde 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: 90.0%

O-methyltetronolide (138194-47-5) → (+)-tetronolide (76705-48-1)

Guidance literature:

With lithium chloride; In dimethyl sulfoxide; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(00)93498-1

Reference yield:

tert-butyl (2E,4E)-octa-2,4,6-trienoate (910042-98-7) → (+)-tetronolide (76705-48-1)

Guidance literature:

Multi-step reaction with 25 steps

1.1: 70 g / K₂CO₃; CH₃SO₂NH₂; quinuclidine / K₂Os₂O₂(OH)4; K₃Fe(CN)6 / 2-methyl-propan-2-ol; H₂O / 6 h / 20 °C

2.1: 43.8 g / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

3.1: 26.8 g / NaBH₄; MeOH / tetrahydrofuran / 3 h / cooling

4.1: AgOTf; Na₂CO₃; 2,6-lutidine / CH₂Cl₂ / 0.33 h / cooling

4.2: CH₂Cl₂ / 16.5 h / -78 - 20 °C

4.3: 10.0 g / toluene / 14 h / 20 °C

5.1: 53 percent / NaHCO₃ / xylene / 114 h / Heating

6.1: 7.7 g / mCPBA; NaH₂PO₄*H₂O / CH₂Cl₂ / 21 h / 0 - 20 °C

7.1: 84 percent / DBU / tetrahydrofuran / 20 h / 20 °C

8.1: 100 percent / TFA / 0.5 h / 20 °C

9.1: ethyl chloroformate; triethylamine / CH₂Cl₂ / 0.5 h / cooling

9.2: 100 percent / NaBH₄; MeOH / tetrahydrofuran / 1.17 h / -40 - 0 °C

10.1: 4.0 g / DMAP; triethylamine / CH₂Cl₂ / 17 h / 0 - 20 °C

11.1: 84 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 26 h / 20 - 40 °C

12.1: 92 percent / Zn-Ag couple; NaHCO₃ / methanol / 18 h / Heating

13.1: 69 percent / xylene / 5 h / Heating; ambient pressure

14.1: 86 percent / pyridinium p-toluenesulfonate / methanol / 14 h / Heating

15.1: 0.14 g / HMPA; NaN(TMS)2 / tetrahydrofuran; toluene / 18 h / -78 - 20 °C

16.1: 0.060 g / MeOH / benzene; petroleum ether / 0.5 h / 0 - 20 °C

17.1: 92 percent / DMP / CH₂Cl₂ / 1.17 h / 0 - 20 °C

18.1: DDQ; water / CH₂Cl₂ / 1 h / 20 °C

18.2: 75 percent / hexachloroacetone; PPh₃ / CH₂Cl₂ / 0.25 h / -40 - -25 °C

19.1: 80 percent / dimethylformamide / 1.5 h / 20 °C

20.1: L-selectride / tetrahydrofuran / 0.37 h / cooling

20.2: 71 percent / iPr₂NEt / CH₂Cl₂ / 15 h / Heating

21.1: TAS-F / acetonitrile / 16 h / Heating

22.1: DMP / CH₂Cl₂ / 1.5 h / 20 °C

23.1: 6.8 mg / aq. HCl / methanol / 1 h / Heating

With Quinuclidine; 2,6-dimethylpyridine; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; phthalic acid dimethyl ester; water; silver trifluoromethanesulfonate; silver; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; L-Selectride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; tris(dimethylamino)sulfonium trimethylsilyldifluoride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; potassium osmate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; xylene; Petroleum ether; tert-butyl alcohol; benzene; 5.1: intramolecular Diels-Alder reactiom / 15.1: Dieckmann condensation;

DOI:10.1021/ja0581346

Reference yield:

C38H52O11 → (+)-tetronolide (76705-48-1)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Heating;

DOI:10.1021/ja0581346

upstream raw materials:

O-methyltetronolide

tert-butyl (E,E)-6-formylpenta-2,4-dienoate

tert-butyl (2E,4E)-octa-2,4,6-trienoate

tert-butyl (E,E)-6,7-dihydroxyocta-2,4-dienoate

Refernces

• 1、 Takeda, Kei,Kawanishi, Eiji,Nakamura, Hitoshi,Yoshii, Eiichi. "Total synthesis of tetronolide, the aglycon of tetrocarcins". . p. 4925 - 4928. Retrieved 2007/10/02.