Isolasalocid A

Base Information

• Chemical Name: Isolasalocid A
• CAS No.: 54156-67-1
• Molecular Formula: C34H54O8
• Molecular Weight: 590.798
• DSSTox Substance ID: DTXSID80969106
• Nikkaji Number: J122.658D
• Wikidata: Q58839832
• Mol file: 54156-67-1.mol

Synonyms:Isolasalocid A;BRN 4218984;54156-67-1;5-19-08-00287 (Beilstein Handbook Reference);Benzoic acid, 6-(7-(2,5-diethyloctahydro-5'-(1-hydroxyethyl)-4-methyl(2,2'-bifuran)-5-yl)-4-hydroxy-3,5-dimethyl-6-oxononyl)-2-hydroxy-3-methyl-, (2S-(2-alpha(2'S*,5'R*(S*)),5-alpha,6-beta(3S*,4R*,5R*,7S*)))-;SCHEMBL11411759;DTXSID80969106;LS-36964;Q58839832;6-{7-[2,5'-Diethyl-5'-(1-hydroxyethyl)-4-methyl[2,2'-bioxolan]-5-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl}-2-hydroxy-3-methylbenzoic acid

Chemical Property of Isolasalocid A

Chemical Property:

• Melting Point: 203°C
• Refractive Index: 1.4900 (estimate)
• Boiling Point: 565.16°C (rough estimate)
• Density: 1.0576 (rough estimate)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 590.38186868
• Heavy Atom Count: 42
• Complexity: 910

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1C(CC(O1)(CC)C2CCC(O2)(CC)C(C)O)C)C(=O)C(C)C(C(C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O
• Isomeric SMILES: CC[C@H]([C@@H]1[C@H](C[C@@](O1)(CC)[C@H]2CC[C@@](O2)(CC)[C@@H](C)O)C)C(=O)[C@@H](C)[C@H]([C@H](C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O

Technology Process of Isolasalocid A

There total 30 articles about Isolasalocid A 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: 98.0%

C48H66O8 (1056032-86-0) → Isolasalocid A (54156-67-1)

Guidance literature:

With Pd(OH)2/C; hydrogen; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1021/ja8040543

Reference yield: 94.0%

Benzyl 23-O-benzyloxymethylisolasalocid A (152934-55-9) → Isolasalocid A (54156-67-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87185-4

Reference yield:

(2S,5R)-2-<(1R)-1-Benzyloxymethoxyethyl>-2-ethyl-5-formyltetrahydrofuran (128531-41-9) → Isolasalocid A (54156-67-1)

Guidance literature:

Multi-step reaction with 17 steps

1: 1) n-BuLi / 1) Et₂O, hexane, 15 min, r.t., 2) Et₂O, hexane, -75 deg C, 2 h

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 3 h

3: 84 percent / Al-Hg / tetrahydrofuran; H₂O / 3 h / Ambient temperature

4: 1) n-BuLi / 1) Et₂O, hexane, -78 deg C, 30 min, 2) Et₂O, 2 h

5: 100 percent / LiAlH₄ / tetrahydrofuran / 0 °C

6: d-camphorsulfonic acid / benzene / Ambient temperature; 1) 30 sec, sonication, 2) 3 h

7: 98 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

8: 1) OsO₄, N-methylmorpholine oxide, 2) Na₂S₂O₄, Celite / 1) acetone, H₂O, 6 h, r.t., 2) H₂O, acetone, overnight, r.t.

9: 95 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature

10: 1) n-BuLi / 1) hexane, THF, 0 deg C, 1 h, 2) THF, r.t., overnight

11: 99 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Ambient temperature

12: 94 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 1.2 h / Ambient temperature

13: 1) Mg / 1) THF, 2) THF, 30 min, -20 deg C

14: 100 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

15: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

17: 94 percent / H₂ / Pd(OH)2 / ethanol / 0.25 h / Ambient temperature

With 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium dithionite; oxalyl dichloride; aluminium amalgam; 3 A molecular sieve; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1016/S0040-4020(01)87185-4

upstream raw materials:

Benzyl 23-O-benzyloxymethylisolasalocid A

(2S,5R)-2-<(1R)-1-Benzyloxymethoxyethyl>-2-ethyl-5-formyltetrahydrofuran

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,3-dioxan-4-yl>propyl phenyl sulfone

(2S)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butan-1-ol

Refernces

• 1、 Horita, Kiyoshi,Noda, Ichio,Tanaka, Kazuhiro,Oikawa, Yuji,Yonemitsu, Osamu. "Stereoselective Total Synthesis of Polyether Ionophore Antibiotics, Isolasalocid A and Lasalocid A. Part 2. The Total Synthesis via Stereoselective Construction of the B Rings by Chelation-Controlled Cyclization under Thermodynamic Conditions". . p. 5997 - 6018. Retrieved 2007/10/02.