CID 6444168

Base Information

• Chemical Name: CID 6444168
• CAS No.: 130595-24-3
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Wikidata: Q104908562
• Metabolomics Workbench ID: 171462
• Mol file: 130595-24-3.mol

Synonyms:CHEMBL372012;BDBM50422599

Chemical Property of CID 6444168

Chemical Property:

• Vapor Pressure: 3.78E-11mmHg at 25°C
• Boiling Point: 478.1°Cat760mmHg
• Flash Point: 243°C
• PSA: 58.92000
• Density: 1.2g/cm³
• LogP: 3.08660
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 623

Purity/Quality:

PHOMACTIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C3=C4C1(CCC(=CCCC(O2)(C(C3(OC4)O)O)C)C)C
• Isomeric SMILES: C[C@@H]1C[C@@H]2C3=C4[C@]1(CC/C(=C/CC[C@](O2)([C@@H]([C@]3(OC4)O)O)C)/C)C

Technology Process of CID 6444168

There total 67 articles about CID 6444168 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: 78.0%

C29H52O4Si2 (501369-42-2) → phomactin A (130595-24-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/ja0296531

Reference yield: 51.0%

C20H28O4 → Sch 49027 + phomactin A (130595-24-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride;

DOI:10.1038/s41557-018-0084-x

Reference yield:

pulegone (89-82-7,90449-51-7) → phomactin A (130595-24-3)

Guidance literature:

Multi-step reaction with 26 steps

1.1: 70 percent / LDA; LiCl

2.1: 75 percent / KOH / Heating

3.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

3.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

4.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

5.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

5.2: diethyl ether; petroleum ether / 1 h / -78 °C

6.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

7.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

7.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

7.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

8.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

9.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

10.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

11.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

12.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

13.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

14.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

14.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

15.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

16.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C

16.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C

17.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C

18.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

18.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C

19.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

20.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

21.1: 25 mg / HCl / 2-methyl-butan-2-ol / 2 h / 20 °C

22.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

23.1: 87 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

24.1: 81 percent / pyridine / CH₂Cl₂ / 0.17 h / -78 °C

25.1: 9-BBN / tetrahydrofuran / 2 h / 40 °C

25.2: 37 percent / thallium carbonate; triphenylarsine / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / tetrahydrofuran; dimethylformamide; H₂O / 12 h / 20 °C

26.1: 78 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; cerium(III) chloride; n-butanethiol; tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; 4-nitro-benzoic acid; chloro-trimethyl-silane; In tetrahydrofuran; methanol; tert-Amyl alcohol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; Petroleum ether; pentane; 16.1: Mitsunobu inversion;

DOI:10.1021/ja0296531

upstream raw materials:

C₂₉H₅₂O₄Si₂

(3R)-6-bromo-2,3-dimethylcyclohexanone

(4S,5R)-2-bromo-3-methoxymethoxymethyl-4,5-dimethyl-4-vinylcyclohex-2-enone

(2R,3R,6E)-[3-(4-iodo-pent-3-enyl)-3-methyloxiranyl]-methanol